Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

Takanori Shibata; Hiroshi Morioka; Shigehisa Tanji; Tadakatsu Hayase; Yasutaka Kodaka; Kenso Soai

doi:10.1016/S0040-4039(96)02031-X

Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

Takanori Shibata, Hiroshi Morioka, Shigehisa Tanji, Tadakatsu Hayase, Yasutaka Kodaka, Kenso Soai^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

Abstract

A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.

Original language	English
Pages (from-to)	8783-8786
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(96)02031-X
Publication status	Published - 1996 Nov 25
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction",

abstract = "A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.",

author = "Takanori Shibata and Hiroshi Morioka and Shigehisa Tanji and Tadakatsu Hayase and Yasutaka Kodaka and Kenso Soai",

note = "Funding Information: Financial support by the New Energy and Industrial Technology Development Organization (NEDO) and by a Grant-in-Aid for Scientific Research from the Ministry and Education, Science, Sports and Culture is gratefully acknowledged.",

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T1 - Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

AU - Shibata, Takanori

AU - Morioka, Hiroshi

AU - Tanji, Shigehisa

AU - Hayase, Tadakatsu

AU - Kodaka, Yasutaka

AU - Soai, Kenso

N1 - Funding Information: Financial support by the New Energy and Industrial Technology Development Organization (NEDO) and by a Grant-in-Aid for Scientific Research from the Ministry and Education, Science, Sports and Culture is gratefully acknowledged.

PY - 1996/11/25

Y1 - 1996/11/25

N2 - A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.

AB - A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.

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DO - 10.1016/S0040-4039(96)02031-X

M3 - Article

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VL - 37

SP - 8783

EP - 8786

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 48

ER -

Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

Abstract

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