A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

Yoshio Ito; Shiro Terashima

doi:10.1016/S0040-4039(00)96931-4

A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

Yoshio Ito, Shiro Terashima

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

15 Citations (Scopus)

Abstract

The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.

Original language	English
Pages (from-to)	6629-6632
Number of pages	4
Journal	Tetrahedron Letters
Volume	28
Issue number	52
DOIs	https://doi.org/10.1016/S0040-4039(00)96931-4
Publication status	Published - Jan 1 1987
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)96931-4

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title = "A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes",

abstract = "The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.",

author = "Yoshio Ito and Shiro Terashima",

year = "1987",

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doi = "10.1016/S0040-4039(00)96931-4",

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journal = "Tetrahedron Letters",

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AU - Ito, Yoshio

AU - Terashima, Shiro

PY - 1987/1/1

Y1 - 1987/1/1

N2 - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.

AB - The title reactions of sterically crowded 2-oxazolidone derivatives with achiral aldehydes in the presence of zinc dust were found to give various 2,3-syn-aldols as major products (at most, 2,3-syn:2,3-anti=98:2). While a 2,3-syn-3,4-syn-aldol could be similarly produced in a highly stereoselective manner, application of the explored reaction to asymmetric synthesis of optically active 2,3-syn-aldols was found to be unpromising.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -

A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

Abstract

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