DOI: 10.1246/cl.1984.1657. COMPLETE RETENTION OF CHIRALITY IN THE PALLADIUM CATALYZED CYCLIZATION OF METHYL (<i>R</i>)-3-OXO-7-(METHOXYCARBONYLOXY)-8-NONENOATE

COMPLETE RETENTION OF CHIRALITY IN THE PALLADIUM CATALYZED CYCLIZATION OF METHYL (R)-3-OXO-7-(METHOXYCARBONYLOXY)-8-NONENOATE

10.1246/cl.1984.1657

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract Optically active methyl (R)-3-oxo-7-(methoxycarbonyloxy)-8-nonenoate (1) underwent intramolecular allylation catalyzed by Pd(OAc)2-dppe in THF at room temperature to give racemic 3-vinyl-2-methoxycarbonylcyclohexanone (3), whereas similar palladium-catalyzed cyclization of a sodium salt of 1 proceeded very rapidly at 0 °C to form optically active 3, indicative of complete retention of the original chiral center.

Bibliography

Yamamoto, K., Deguchi, R., Ogimura, Y., & Tsuji, J. (1984). COMPLETE RETENTION OF CHIRALITY IN THE PALLADIUM CATALYZED CYCLIZATION OF METHYL (R)-3-OXO-7-(METHOXYCARBONYLOXY)-8-NONENOATE. Chemistry Letters, 13(10), 1657â1660.

Authors 4

Keiji Yamamoto (first)
Ryoji Deguchi (additional)
Yoshinobu Ogimura (additional)
Jiro Tsuji (additional)

References 12 Referenced 20

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10.1016/0040-4020(77)80284-6
10.1021/ar50155a001
10.1016/S0040-4039(00)85719-6
10.5059/yukigoseikyokaishi.41.619
10.1016/S0040-4039(00)87540-1
10.1021/ja00467a047
10.1351/pac198254010189
10.1021/ja00740a011
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{'key': '2024011915104115800_r12'}

Dates

Type	When
Created	19 years, 1 month ago (July 24, 2006, 10:45 p.m.)
Deposited	1 year, 7 months ago (Jan. 19, 2024, 10:10 a.m.)
Indexed	1 year, 7 months ago (Jan. 19, 2024, 7:03 p.m.)
Issued	40 years, 11 months ago (Oct. 1, 1984)
Published	40 years, 11 months ago (Oct. 1, 1984)
Published Online	19 years, 5 months ago (March 27, 2006)
Published Print	40 years, 11 months ago (Oct. 5, 1984)

Funders 0

None

BibTeX

@article{Yamamoto_1984, title={COMPLETE RETENTION OF CHIRALITY IN THE PALLADIUM CATALYZED CYCLIZATION OF METHYL (R)-3-OXO-7-(METHOXYCARBONYLOXY)-8-NONENOATE}, volume={13}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1984.1657}, DOI={10.1246/cl.1984.1657}, number={10}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Yamamoto, Keiji and Deguchi, Ryoji and Ogimura, Yoshinobu and Tsuji, Jiro}, year={1984}, month=oct, pages={1657–1660} }

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