An efficient synthesis of (2S)- and (2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one

A.L.J. Beckwith; S.G. Pyne; B. Dikic; C.L.L. Chai; P.A. Gordon; Brian Skelton; M.J. Tozer; Allan White

doi:10.1071/CH9931425

An efficient synthesis of (2S)- and (2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one

A.L.J. Beckwith
, S.G. Pyne
, B. Dikic
, C.L.L. Chai
, P.A. Gordon
, Brian Skelton
, M.J. Tozer
, Allan White

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

16 Citations (Scopus)

Abstract

An efficient synthesis of the title compounds in high enantiomeric purity (>98%) involves bromination under photolytic conditions of (2S)- or (2R)-oxazolidinones derived from (S)-alanine followed by treatment of the products with sodium iodide in refluxing acetone. A room-temperature single-crystal X-ray study of (2S,4Z)-N-benzoyl-4-bromomethylene-2-t-butyloxazolidin-5-one is recorded.

Original language	English
Pages (from-to)	1425-1430
Journal	Australian Journal of Chemistry: an international journal for chemical science
Volume	46
DOIs	https://doi.org/10.1071/CH9931425
Publication status	Published - 1993

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10.1071/CH9931425

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title = "An efficient synthesis of (2S)- and (2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one",

abstract = "An efficient synthesis of the title compounds in high enantiomeric purity (>98\%) involves bromination under photolytic conditions of (2S)- or (2R)-oxazolidinones derived from (S)-alanine followed by treatment of the products with sodium iodide in refluxing acetone. A room-temperature single-crystal X-ray study of (2S,4Z)-N-benzoyl-4-bromomethylene-2-t-butyloxazolidin-5-one is recorded.",

author = "A.L.J. Beckwith and S.G. Pyne and B. Dikic and C.L.L. Chai and P.A. Gordon and Brian Skelton and M.J. Tozer and Allan White",

year = "1993",

doi = "10.1071/CH9931425",

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volume = "46",

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journal = "Australian Journal of Chemistry: an international journal for chemical science",

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T1 - An efficient synthesis of (2S)- and (2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one

AU - Beckwith, A.L.J.

AU - Pyne, S.G.

AU - Dikic, B.

AU - Chai, C.L.L.

AU - Gordon, P.A.

AU - Skelton, Brian

AU - Tozer, M.J.

AU - White, Allan

PY - 1993

Y1 - 1993

N2 - An efficient synthesis of the title compounds in high enantiomeric purity (>98%) involves bromination under photolytic conditions of (2S)- or (2R)-oxazolidinones derived from (S)-alanine followed by treatment of the products with sodium iodide in refluxing acetone. A room-temperature single-crystal X-ray study of (2S,4Z)-N-benzoyl-4-bromomethylene-2-t-butyloxazolidin-5-one is recorded.

AB - An efficient synthesis of the title compounds in high enantiomeric purity (>98%) involves bromination under photolytic conditions of (2S)- or (2R)-oxazolidinones derived from (S)-alanine followed by treatment of the products with sodium iodide in refluxing acetone. A room-temperature single-crystal X-ray study of (2S,4Z)-N-benzoyl-4-bromomethylene-2-t-butyloxazolidin-5-one is recorded.

U2 - 10.1071/CH9931425

DO - 10.1071/CH9931425

M3 - Article

SN - 0004-9425

VL - 46

SP - 1425

EP - 1430

JO - Australian Journal of Chemistry: an international journal for chemical science

JF - Australian Journal of Chemistry: an international journal for chemical science

ER -

An efficient synthesis of (2S)- and (2R)-N-benzoyl-2-t-butyl-4-methyleneoxazolidin-5-one

Abstract

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