Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

Jonathan Clayden; Eric W. Collington; R. Brian Lamount; Stuart Warren

doi:10.1016/S0040-4039(00)60383-0

Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

Jonathan Clayden^*
, Eric W. Collington
, R. Brian Lamount
, Stuart Warren

^*Corresponding author for this work

School of Chemistry

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

32 Citations (Scopus)

Abstract

Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

Original language	English
Pages (from-to)	2203-2206
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	13
DOIs	https://doi.org/10.1016/S0040-4039(00)60383-0
Publication status	Published - 26 Mar 1993

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Organic & Biological

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@article{6ca01feb442247b68ada1790ede0f6b2,

title = "Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond",

abstract = "Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.",

author = "Jonathan Clayden and Collington, \{Eric W.\} and Lamount, \{R. Brian\} and Stuart Warren",

year = "1993",

month = mar,

day = "26",

doi = "10.1016/S0040-4039(00)60383-0",

language = "English",

volume = "34",

pages = "2203--2206",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "13",

}

Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond. / Clayden, Jonathan; Collington, Eric W.; Lamount, R. Brian et al.
In: Tetrahedron Letters, Vol. 34, No. 13, 26.03.1993, p. 2203-2206.

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

TY - JOUR

T1 - Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides

T2 - Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

AU - Clayden, Jonathan

AU - Collington, Eric W.

AU - Lamount, R. Brian

AU - Warren, Stuart

PY - 1993/3/26

Y1 - 1993/3/26

N2 - Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

AB - Alkenyl oxazolidinones 5 have been made from the urethane derivatives 4 diphenylphosphinoyl epoxy alcohols 1 by a tandem intramolecular ring closure - Horner-Wittig elimination sequence. The stereoisomers of diphenylphosphinoyl epoxy alcohols containing further chiral centres have been made by enantio- and diastereoselective epoxidation, and converted stereospecifically to alkenyl oxazolidinones with 1,4-related chiral centres across a controlled geometry double bond.

UR - https://www.scopus.com/pages/publications/0027512041

U2 - 10.1016/S0040-4039(00)60383-0

DO - 10.1016/S0040-4039(00)60383-0

M3 - Article (Academic Journal)

AN - SCOPUS:0027512041

SN - 0040-4039

VL - 34

SP - 2203

EP - 2206

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Alkenyl oxazolidinones by stereoselective epoxidation of δ-hydroxy allylic phosphine oxides: Synthesis of any isomer (RR, RS, SR or SS; E or Z) bearing 1,4-related chiral centres across a double bond

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