A Michael addition and alkylation sequence using m methyl 2-(trimethylsily)-propenoate. Stereoselective synthesis of α-silyl esters

J. Tanaka, S. Kanemasa, Y. Ninomiya, O. Tsuge

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Michael addition of organomagnesiums or -lithiums with methyl 2-(trimethylsilyl)propenoate leads to either 1:1 or 1:2 adduct anions, depending upon the reaction condition and the reactivity of donor molecules. The adduct anions, both 1:1 and 1:2 types, are quenched with alkyl halides or water in a highly stereoselective manner to produce α-silylated esters. A rigid intramolecular chelation working in the adduct anions is partly responsible for the high selectivity.

Original languageEnglish
Pages (from-to)476-483
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume63
Issue number2
DOIs
Publication statusPublished - Jul 25 1990

Fingerprint

Alkylation
Anions
Esters
Chelation
Molecules
Water

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

A Michael addition and alkylation sequence using m methyl 2-(trimethylsily)-propenoate. Stereoselective synthesis of α-silyl esters. / Tanaka, J.; Kanemasa, S.; Ninomiya, Y.; Tsuge, O.

In: Bulletin of the Chemical Society of Japan, Vol. 63, No. 2, 25.07.1990, p. 476-483.

Research output: Contribution to journalArticle

@article{42f120aa4f9e4d09a58d2c23eefad77b,
title = "A Michael addition and alkylation sequence using m methyl 2-(trimethylsily)-propenoate. Stereoselective synthesis of α-silyl esters",
abstract = "Michael addition of organomagnesiums or -lithiums with methyl 2-(trimethylsilyl)propenoate leads to either 1:1 or 1:2 adduct anions, depending upon the reaction condition and the reactivity of donor molecules. The adduct anions, both 1:1 and 1:2 types, are quenched with alkyl halides or water in a highly stereoselective manner to produce α-silylated esters. A rigid intramolecular chelation working in the adduct anions is partly responsible for the high selectivity.",
author = "J. Tanaka and S. Kanemasa and Y. Ninomiya and O. Tsuge",
year = "1990",
month = "7",
day = "25",
doi = "10.1246/bcsj.63.476",
language = "English",
volume = "63",
pages = "476--483",
journal = "Bulletin of the Chemical Society of Japan",
issn = "0009-2673",
publisher = "The Chemical Society of Japan",
number = "2",

}

TY - JOUR

T1 - A Michael addition and alkylation sequence using m methyl 2-(trimethylsily)-propenoate. Stereoselective synthesis of α-silyl esters

AU - Tanaka, J.

AU - Kanemasa, S.

AU - Ninomiya, Y.

AU - Tsuge, O.

PY - 1990/7/25

Y1 - 1990/7/25

N2 - Michael addition of organomagnesiums or -lithiums with methyl 2-(trimethylsilyl)propenoate leads to either 1:1 or 1:2 adduct anions, depending upon the reaction condition and the reactivity of donor molecules. The adduct anions, both 1:1 and 1:2 types, are quenched with alkyl halides or water in a highly stereoselective manner to produce α-silylated esters. A rigid intramolecular chelation working in the adduct anions is partly responsible for the high selectivity.

AB - Michael addition of organomagnesiums or -lithiums with methyl 2-(trimethylsilyl)propenoate leads to either 1:1 or 1:2 adduct anions, depending upon the reaction condition and the reactivity of donor molecules. The adduct anions, both 1:1 and 1:2 types, are quenched with alkyl halides or water in a highly stereoselective manner to produce α-silylated esters. A rigid intramolecular chelation working in the adduct anions is partly responsible for the high selectivity.

UR - http://www.scopus.com/inward/record.url?scp=0025024504&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025024504&partnerID=8YFLogxK

U2 - 10.1246/bcsj.63.476

DO - 10.1246/bcsj.63.476

M3 - Article

AN - SCOPUS:0025024504

VL - 63

SP - 476

EP - 483

JO - Bulletin of the Chemical Society of Japan

JF - Bulletin of the Chemical Society of Japan

SN - 0009-2673

IS - 2

ER -