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

Access to Document

10.1016/S0040-4039(00)96931-4

Fingerprint Dive into the research topics of 'A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes'. Together they form a unique fingerprint.

Cite this

@article{bf47fac121f0409fade34bdbe3c239f3,

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",

month = jan,

day = "1",

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

language = "English",

volume = "28",

pages = "6629--6632",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "52",

}

TY - JOUR

T1 - A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

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.

UR - http://www.scopus.com/inward/record.url?scp=0001439535&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001439535&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)96931-4

DO - 10.1016/S0040-4039(00)96931-4

M3 - Article

AN - SCOPUS:0001439535

VL - 28

SP - 6629

EP - 6632

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -