DOI: 10.1246/bcsj.61.1213. Metal(II) <i>d</i>-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles

Metal(II) d-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles

10.1246/bcsj.61.1213

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartrates as heterogeneous chiral Lewis acid catalysts. The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartrate, and Zn(II) d-tartrate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42% ee, respectively. Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tartrate was studied.

Bibliography

Yamashita, H. (1988). Metal(II) d-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles. Bulletin of the Chemical Society of Japan, 61(4), 1213â1220.

Authors 1

Hiroyuki Yamashita (first)

References 53 Referenced 88

10.1016/S0040-4039(01)82939-7
{'key': '2024011810403712600_r2'}
{'key': '2024011810403712600_r3'}
{'key': '2024011810403712600_r4'}
{'key': '2024011810403712600_r5'}
10.1016/S0040-4039(01)80881-9
10.1016/S0040-4020(01)90599-X
{'key': '2024011810403712600_r8'}
{'key': '2024011810403712600_r9'}
{'key': '2024011810403712600_r10'}
{'key': '2024011810403712600_r11'}
{'key': '2024011810403712600_r12'}
{'key': '2024011810403712600_r13'}
{'key': '2024011810403712600_r14'}
10.1039/CT9160900235
10.1002/cber.19030360405
{'key': '2024011810403712600_r17'}
10.1039/CT9160900235
10.1021/ja01182a095
{'key': '2024011810403712600_r20'}
10.1021/ja02046a007
10.1039/CT8997500725
10.1002/zaac.19362270204
10.1002/zaac.19362270408
10.1246/bcsj.47.1945
{'key': '2024011810403712600_r26'}
10.1002/hlca.19760590702
10.1246/bcsj.60.1813
10.1002/hlca.19700530409
{'key': '2024011810403712600_r30'}
{'key': '2024011810403712600_r31'}
10.1021/jo01266a124
10.1248/cpb.23.2539
{'key': '2024011810403712600_r34'}
{'key': '2024011810403712600_r35'}
10.1016/S0040-4039(00)88278-7
10.1021/ja01530a065
10.1021/jo01060a605
{'key': '2024011810403712600_r39'}
10.1021/jo01261a013
10.1021/ja00803a034
10.1002/hlca.19820650339
10.1107/S0567740868004619
10.1107/S0567740882009042
{'key': '2024011810403712600_r45'}
10.1021/ic00183a017
10.1135/cccc19641418
10.1135/cccc19650777
10.1002/ange.19650770904
10.1246/bcsj.36.459
10.1246/bcsj.39.1235
10.1139/v77-592
10.1021/ja01124a023

Dates

Type	When
Created	19 years ago (July 25, 2006, 5:50 p.m.)
Deposited	1 year, 7 months ago (Jan. 18, 2024, 12:40 a.m.)
Indexed	2 weeks, 1 day ago (Aug. 7, 2025, 4:59 p.m.)
Issued	37 years, 4 months ago (April 1, 1988)
Published	37 years, 4 months ago (April 1, 1988)
Published Online	19 years, 1 month ago (June 27, 2006)
Published Print	37 years, 4 months ago (April 1, 1988)

Funders 0

None

BibTeX

@article{Yamashita_1988, title={Metal(II) d-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles}, volume={61}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.61.1213}, DOI={10.1246/bcsj.61.1213}, number={4}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Yamashita, Hiroyuki}, year={1988}, month=apr, pages={1213–1220} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        7
      ]
    ],
    "date-time": "2025-08-07T20:59:06Z",
    "timestamp": 1754600346882
  },
  "reference-count": 53,
  "publisher": "Oxford University Press (OUP)",
  "issue": "4",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            1988,
            4,
            1
          ]
        ],
        "date-time": "1988-04-01T00:00:00Z",
        "timestamp": 575856000000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "https://academic.oup.com/pages/standard-publication-reuse-rights"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1988,
        4,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title>\n               <jats:p>The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartrates as heterogeneous chiral Lewis acid catalysts. The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartrate, and Zn(II) d-tartrate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42% ee, respectively. Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tartrate was studied.</jats:p>",
  "DOI": "10.1246/bcsj.61.1213",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2006,
        7,
        25
      ]
    ],
    "date-time": "2006-07-25T21:50:38Z",
    "timestamp": 1153864238000
  },
  "page": "1213-1220",
  "source": "Crossref",
  "is-referenced-by-count": 88,
  "title": "Metal(II) <i>d</i>-Tartrates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles",
  "prefix": "10.1093",
  "volume": "61",
  "author": [
    {
      "given": "Hiroyuki",
      "family": "Yamashita",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Central Research Institute, Mitsui Toatsu Chemicals, INC"
        }
      ]
    }
  ],
  "member": "286",
  "published-online": {
    "date-parts": [
      [
        2006,
        6,
        27
      ]
    ]
  },
  "reference": [
    {
      "key": "2024011810403712600_r1",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(01)82939-7"
    },
    {
      "key": "2024011810403712600_r2"
    },
    {
      "key": "2024011810403712600_r3"
    },
    {
      "key": "2024011810403712600_r4"
    },
    {
      "key": "2024011810403712600_r5"
    },
    {
      "key": "2024011810403712600_r6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(01)80881-9"
    },
    {
      "key": "2024011810403712600_r7",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(01)90599-X"
    },
    {
      "key": "2024011810403712600_r8"
    },
    {
      "key": "2024011810403712600_r9"
    },
    {
      "key": "2024011810403712600_r10"
    },
    {
      "key": "2024011810403712600_r11"
    },
    {
      "key": "2024011810403712600_r12"
    },
    {
      "key": "2024011810403712600_r13"
    },
    {
      "key": "2024011810403712600_r14"
    },
    {
      "key": "2024011810403712600_r15",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/CT9160900235"
    },
    {
      "key": "2024011810403712600_r16",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/cber.19030360405"
    },
    {
      "key": "2024011810403712600_r17"
    },
    {
      "key": "2024011810403712600_r18",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/CT9160900235"
    },
    {
      "key": "2024011810403712600_r19",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01182a095"
    },
    {
      "key": "2024011810403712600_r20"
    },
    {
      "key": "2024011810403712600_r21",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja02046a007"
    },
    {
      "key": "2024011810403712600_r22",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/CT8997500725"
    },
    {
      "key": "2024011810403712600_r23",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/zaac.19362270204"
    },
    {
      "key": "2024011810403712600_r24",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/zaac.19362270408"
    },
    {
      "key": "2024011810403712600_r25",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.47.1945"
    },
    {
      "key": "2024011810403712600_r26"
    },
    {
      "key": "2024011810403712600_r27",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/hlca.19760590702"
    },
    {
      "key": "2024011810403712600_r28",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.60.1813"
    },
    {
      "key": "2024011810403712600_r29",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/hlca.19700530409"
    },
    {
      "key": "2024011810403712600_r30"
    },
    {
      "key": "2024011810403712600_r31"
    },
    {
      "key": "2024011810403712600_r32",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01266a124"
    },
    {
      "key": "2024011810403712600_r33",
      "doi-asserted-by": "publisher",
      "DOI": "10.1248/cpb.23.2539"
    },
    {
      "key": "2024011810403712600_r34"
    },
    {
      "key": "2024011810403712600_r35"
    },
    {
      "key": "2024011810403712600_r36",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)88278-7"
    },
    {
      "key": "2024011810403712600_r37",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01530a065"
    },
    {
      "key": "2024011810403712600_r38",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01060a605"
    },
    {
      "key": "2024011810403712600_r39"
    },
    {
      "key": "2024011810403712600_r40",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01261a013"
    },
    {
      "key": "2024011810403712600_r41",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00803a034"
    },
    {
      "key": "2024011810403712600_r42",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/hlca.19820650339"
    },
    {
      "key": "2024011810403712600_r43",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0567740868004619"
    },
    {
      "key": "2024011810403712600_r44",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0567740882009042"
    },
    {
      "key": "2024011810403712600_r45"
    },
    {
      "key": "2024011810403712600_r46",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00183a017"
    },
    {
      "key": "2024011810403712600_r47",
      "doi-asserted-by": "publisher",
      "DOI": "10.1135/cccc19641418"
    },
    {
      "key": "2024011810403712600_r48",
      "doi-asserted-by": "publisher",
      "DOI": "10.1135/cccc19650777"
    },
    {
      "key": "2024011810403712600_r49",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19650770904"
    },
    {
      "key": "2024011810403712600_r50",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.36.459"
    },
    {
      "key": "2024011810403712600_r51",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.39.1235"
    },
    {
      "key": "2024011810403712600_r52",
      "doi-asserted-by": "publisher",
      "DOI": "10.1139/v77-592"
    },
    {
      "key": "2024011810403712600_r53",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01124a023"
    }
  ],
  "container-title": "Bulletin of the Chemical Society of Japan",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/61/4/1213/55723867/bcsj.61.1213.pdf",
      "content-type": "application/pdf",
      "content-version": "vor",
      "intended-application": "syndication"
    },
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/61/4/1213/55723867/bcsj.61.1213.pdf",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        18
      ]
    ],
    "date-time": "2024-01-18T05:40:45Z",
    "timestamp": 1705556445000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://academic.oup.com/bcsj/article/61/4/1213/7365262"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1988,
        4,
        1
      ]
    ]
  },
  "references-count": 53,
  "journal-issue": {
    "issue": "4",
    "published-online": {
      "date-parts": [
        [
          2006,
          6,
          27
        ]
      ]
    },
    "published-print": {
      "date-parts": [
        [
          1988,
          4,
          1
        ]
      ]
    }
  },
  "URL": "http://dx.doi.org/10.1246/bcsj.61.1213",
  "relation": {},
  "ISSN": [
    "0009-2673",
    "1348-0634"
  ],
  "subject": [],
  "published-other": {
    "date-parts": [
      [
        1988,
        4
      ]
    ]
  },
  "published": {
    "date-parts": [
      [
        1988,
        4,
        1
      ]
    ]
  }
}