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

Antonio Romero, Keith Woerpel

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)2127-2130
Number of pages4
JournalOrganic Letters
Volume8
Issue number10
DOIs
StatePublished - May 11 2006

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Silanes
Lactams
isocyanates
silanes
acetals
synthesis
Acetals
substitutes
oxidation
Substitution reactions
Oxidation
chlorosulfonyl isocyanate

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate. / Romero, Antonio; Woerpel, Keith.

In: Organic Letters, Vol. 8, No. 10, 11.05.2006, p. 2127-2130.

Research output: Contribution to journalArticle

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