Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

Antonio Romero; K. A. Woerpel

doi:10.1021/ol060596g

Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

Antonio Romero, K. A. Woerpel

Chemistry

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

Abstract

A stereoselective synthesis of γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO ₂NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted γ-lactams. Oxidation of the silyl group afforded access to complex β-hydroxy-γ-lactams.

Original language	English (US)
Pages (from-to)	2127-2130
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol060596g
State	Published - May 11 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol060596g

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abstract = "A stereoselective synthesis of γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO 2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted γ-lactams. Oxidation of the silyl group afforded access to complex β-hydroxy-γ-lactams.",

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AB - A stereoselective synthesis of γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO 2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted γ-lactams. Oxidation of the silyl group afforded access to complex β-hydroxy-γ-lactams.

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Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

Abstract

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