DOI: 10.1246/bcsj.52.3371. Enantioface-differentiating Reactions Using (2S,2′S)-2-Hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines as Chiral Ligands. Addition of Lithium Derivatives of Methyl Phenyl Sulfide, Acetonitrile, N-Nitrosodimethylamine, and 2-Methylthiothiazoline to Aldehydes

Enantioface-differentiating Reactions Using (2S,2′S)-2-Hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines as Chiral Ligands. Addition of Lithium Derivatives of Methyl Phenyl Sulfide, Acetonitrile, N-Nitrosodimethylamine, and 2-Methylthiothiazoline to Aldehydes

10.1246/bcsj.52.3371

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Optically active oxiranes, β-hydroxy nitrile, β-Hiydroxy N-nitrosoamine, and thiirane were obtained (up to 72% optical purity) by the enantioface-differentiating addition of lithium derivatives of methyl phenyl sulfide, acetonitrile, N-nitrosodimethylamine, and 2-methylthiothiazoline to aldehydes using (2S,2′S)-2-hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines (1a–f) as chiral ligands. Optical purity of the products depended greatly on the reaction medium (dimethoxymethane or dimethyl ether gave the best results) and the structure of pyrrolidine moieties of 1a–f.)

Authors 2

Kenso Soai (first)
Teruaki Mukaiyama (additional)

References 33 Referenced 54

{'key': '2024011715093723300_r1'}
{'key': '2024011715093723300_r2'}
10.1021/ja00467a047
10.1246/bcsj.51.1869
10.1002/hlca.19770600202
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{'key': '2024011715093723300_r7'}
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10.1021/ja00500a015
{'key': '2024011715093723300_r10'}
{'key': '2024011715093723300_r11'}
10.1021/ja00791a084
10.1021/ja00803a034
{'key': '2024011715093723300_r14'}
10.1021/jo00432a009
{'key': '2024011715093723300_r16'}
10.1021/ja00803a034
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10.1021/ja00448a059
{'key': '2024011715093723300_r20'}
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{'key': '2024011715093723300_r22'}
10.1021/jo00872a015
{'key': '2024011715093723300_r24'}
10.1021/jo01350a052
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{'key': '2024011715093723300_r27'}
{'key': '2024011715093723300_r28'}
{'key': '2024011715093723300_r29'}
{'key': '2024011715093723300_r30'}
10.1021/ja00783a034
{'key': '2024011715093723300_r32'}
10.1248/cpb.20.2067

Dates

Type	When
Created	19 years, 1 month ago (July 19, 2006, 7:13 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 8:19 a.m.)
Indexed	1 year, 7 months ago (Jan. 21, 2024, 7:59 a.m.)
Issued	45 years, 10 months ago (Nov. 1, 1979)
Published	45 years, 10 months ago (Nov. 1, 1979)
Published Online	19 years, 4 months ago (April 19, 2006)
Published Print	45 years, 10 months ago (Nov. 1, 1979)

Funders 0

None

BibTeX

@article{Soai_1979, title={Enantioface-differentiating Reactions Using (2S,2′S)-2-Hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines as Chiral Ligands. Addition of Lithium Derivatives of Methyl Phenyl Sulfide, Acetonitrile, N-Nitrosodimethylamine, and 2-Methylthiothiazoline to Aldehydes}, volume={52}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.52.3371}, DOI={10.1246/bcsj.52.3371}, number={11}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Soai, Kenso and Mukaiyama, Teruaki}, year={1979}, month=nov, pages={3371–3376} }

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