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

Mari C.M. Higginbotham; Lorna Kennedy; Anita G. Lindsay; Andreas Troester; Magnus W.P. 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 C.M. Higginbotham, Lorna Kennedy, Anita G. Lindsay, Andreas Troester, Magnus W.P. Bebbington

Chemistry and Biochemistry

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

8 Scopus citations

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
DOIs	https://doi.org/10.1016/j.tet.2014.11.058
State	Published - 28 Jan 2015

Keywords

Allenes
Gold catalysis
Hydroamination
Sulfamidates

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10.1016/j.tet.2014.11.058

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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 = "Allenes, Gold catalysis, Hydroamination, Sulfamidates",

author = "Higginbotham, {Mari C.M.} and Lorna Kennedy and Lindsay, {Anita G.} and Andreas Troester and Bebbington, {Magnus W.P.}",

note = "Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd.",

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T2 - Current scope, stereochemistry and competing ene-allene cycloisomerisation

AU - Higginbotham, Mari C.M.

AU - Kennedy, Lorna

AU - Lindsay, Anita G.

AU - Troester, Andreas

AU - Bebbington, Magnus W.P.

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 - Allenes

KW - Gold catalysis

KW - Hydroamination

KW - Sulfamidates

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U2 - 10.1016/j.tet.2014.11.058

DO - 10.1016/j.tet.2014.11.058

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JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

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

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Keywords

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