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

Antonio Romero; Keith 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, Keith Woerpel

Chemistry

Research output: Contribution to journal › Article

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

Fingerprint

Silanes

Lactams

isocyanates

silanes

acetals

synthesis

Acetals

substitutes

oxidation

Substitution reactions

Oxidation

chlorosulfonyl isocyanate

ASJC Scopus subject areas

Molecular Medicine

Cite this

Romero, A., & Woerpel, K. (2006). Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate. Organic Letters, 8(10), 2127-2130. https://doi.org/10.1021/ol060596g

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 journal › Article

Romero, A & Woerpel, K 2006, 'Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate', Organic Letters, vol. 8, no. 10, pp. 2127-2130. https://doi.org/10.1021/ol060596g

Romero A, Woerpel K. Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate. Organic Letters. 2006 May 11;8(10):2127-2130. https://doi.org/10.1021/ol060596g

Romero, Antonio ; Woerpel, Keith. / Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate. In: Organic Letters. 2006 ; Vol. 8, No. 10. pp. 2127-2130.

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Access to Document

10.1021/ol060596g