Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

Mark P. Gamble; Gerard M.P. Giblin; John G. Montana; Peter O'Brien; Timothy P. Ockendon; Richard J.K. Taylor

doi:10.1016/0040-4039(96)01610-3

Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

Mark P. Gamble, Gerard M.P. Giblin, John G. Montana, Peter O'Brien, Timothy P. Ockendon, Richard J.K. Taylor

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

Abstract

Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsilyl)amide. Ramberg-Backlund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.

Original language	English
Pages (from-to)	7457-7460
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	41
DOIs	https://doi.org/10.1016/0040-4039(96)01610-3
Publication status	Published - 7 Oct 1996

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abstract = "Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsilyl)amide. Ramberg-Backlund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.",

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T1 - Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

AU - Gamble, Mark P.

AU - Giblin, Gerard M.P.

AU - Montana, John G.

AU - O'Brien, Peter

AU - Ockendon, Timothy P.

AU - Taylor, Richard J.K.

PY - 1996/10/7

Y1 - 1996/10/7

N2 - Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsilyl)amide. Ramberg-Backlund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.

AB - Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsilyl)amide. Ramberg-Backlund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.

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U2 - 10.1016/0040-4039(96)01610-3

DO - 10.1016/0040-4039(96)01610-3

M3 - Article

AN - SCOPUS:16044364084

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone

Abstract

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