Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation

Mari Higginbotham; Lorna Kennedy; Anita Lindsay; Andreas Troester; Magnus William Paul Bebbington

doi:10.1016/j.tet.2014.11.058

Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation

Mari Higginbotham, Lorna Kennedy, Anita Lindsay, Andreas Troester, Magnus William Paul Bebbington

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Abstract

Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process.

Original language	English
Pages (from-to)	727-737
Number of pages	11
Journal	Tetrahedron
Volume	71
Issue number	4
Early online date	5 Dec 2014
DOIs	https://doi.org/10.1016/j.tet.2014.11.058
Publication status	Published - 28 Jan 2015

Keywords

gold catalysis
hydroamination
allenes
sulfamidates

ASJC Scopus subject areas

General Chemistry

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10.1016/j.tet.2014.11.058

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Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation
Bebbington, M. W. P. (Creator), Heriot-Watt University, 9 Jul 2015
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title = "Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation",

abstract = "Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process. ",

keywords = "gold catalysis, hydroamination, allenes, sulfamidates",

author = "Mari Higginbotham and Lorna Kennedy and Anita Lindsay and Andreas Troester and Bebbington, {Magnus William Paul}",

note = "The authors thank the Engineering and Physical Sciences Research Council (for a DTA to M.C.M.H. and for funding to L.K. (Grant 736 M.C.M. Higginbotham et al. / Tetrahedron 71 (2015) 727e737",

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AU - Higginbotham, Mari

AU - Kennedy, Lorna

AU - Lindsay, Anita

AU - Troester, Andreas

AU - Bebbington, Magnus William Paul

N1 - The authors thank the Engineering and Physical Sciences Research Council (for a DTA to M.C.M.H. and for funding to L.K. (Grant 736 M.C.M. Higginbotham et al. / Tetrahedron 71 (2015) 727e737

PY - 2015/1/28

Y1 - 2015/1/28

N2 - Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process.

AB - Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process.

KW - gold catalysis

KW - hydroamination

KW - allenes

KW - sulfamidates

U2 - 10.1016/j.tet.2014.11.058

DO - 10.1016/j.tet.2014.11.058

M3 - Article

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VL - 71

SP - 727

EP - 737

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation

Abstract

Keywords

ASJC Scopus subject areas

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Gold(I)-catalysed synthesis of cyclic sulfamidates : current scope, stereochemistry and competing ene-allene cycloisomerisation

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