Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides

Jonathan Clayden; Eric W. Collington; Stuart Warren

doi:10.1016/S0040-4039(00)91787-8

Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides

Jonathan Clayden^*, Eric W. Collington, Stuart Warren

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

24 Citations (Scopus)

Abstract

Epoxidation of δ-hydroxy allylic phosphine oxides 5 with m-CPBA can be syn selective. All stereoisomers of epoxy alcohols 6 are available when this method is used in tandem with an anti selective Sharpless kinetic resolution. The stereoisomers of epoxy alcohols 6 can be transformed stereospecifically into single isomers of unsaturated α-amino acids 7. A mechanistic explanation for the stereoselectivity observed in the m-CPBA epoxidation is proposed.

Original language	English
Pages (from-to)	1327-1330
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(00)91787-8
Publication status	Published - 19 Feb 1993

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title = "Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides",

abstract = "Epoxidation of δ-hydroxy allylic phosphine oxides 5 with m-CPBA can be syn selective. All stereoisomers of epoxy alcohols 6 are available when this method is used in tandem with an anti selective Sharpless kinetic resolution. The stereoisomers of epoxy alcohols 6 can be transformed stereospecifically into single isomers of unsaturated α-amino acids 7. A mechanistic explanation for the stereoselectivity observed in the m-CPBA epoxidation is proposed.",

author = "Jonathan Clayden and Collington, {Eric W.} and Stuart Warren",

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T1 - Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides

AU - Clayden, Jonathan

AU - Collington, Eric W.

AU - Warren, Stuart

PY - 1993/2/19

Y1 - 1993/2/19

N2 - Epoxidation of δ-hydroxy allylic phosphine oxides 5 with m-CPBA can be syn selective. All stereoisomers of epoxy alcohols 6 are available when this method is used in tandem with an anti selective Sharpless kinetic resolution. The stereoisomers of epoxy alcohols 6 can be transformed stereospecifically into single isomers of unsaturated α-amino acids 7. A mechanistic explanation for the stereoselectivity observed in the m-CPBA epoxidation is proposed.

AB - Epoxidation of δ-hydroxy allylic phosphine oxides 5 with m-CPBA can be syn selective. All stereoisomers of epoxy alcohols 6 are available when this method is used in tandem with an anti selective Sharpless kinetic resolution. The stereoisomers of epoxy alcohols 6 can be transformed stereospecifically into single isomers of unsaturated α-amino acids 7. A mechanistic explanation for the stereoselectivity observed in the m-CPBA epoxidation is proposed.

UR - http://www.scopus.com/inward/record.url?scp=0027393932&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)91787-8

DO - 10.1016/S0040-4039(00)91787-8

M3 - Article (Academic Journal)

AN - SCOPUS:0027393932

VL - 34

SP - 1327

EP - 1330

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -

Stereocontrolled synthesis of R or S E or Z unsaturated α-amino acids by enantio- and diastereoselective epoxidation of δ-hydroxy allylic phosphine oxides

Abstract

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