Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Koichi Mikami; Teck Peng Loh; Takeshi Nakai

doi:10.1016/S0040-4039(00)82332-1

Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Koichi Mikami, Teck Peng Loh, Takeshi Nakai

Institute of Science Tokyo

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

49 Scopus citations

Abstract

Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

Original language	English
Pages (from-to)	6305-6308
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(00)82332-1
State	Published - 1988
Externally published	Yes

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title = "Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain",

abstract = "Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.",

author = "Koichi Mikami and Loh, {Teck Peng} and Takeshi Nakai",

year = "1988",

doi = "10.1016/S0040-4039(00)82332-1",

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AU - Mikami, Koichi

AU - Loh, Teck Peng

AU - Nakai, Takeshi

PY - 1988

Y1 - 1988

N2 - Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

AB - Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain.

UR - http://www.scopus.com/inward/record.url?scp=0001733480&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)82332-1

DO - 10.1016/S0040-4039(00)82332-1

M3 - 文章

AN - SCOPUS:0001733480

SN - 0040-4039

VL - 29

SP - 6305

EP - 6308

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain

Abstract

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