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.

@article{42da230ef0c2444cac7d9d0d70287c65,

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

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.",

author = "Antonio Romero and Keith Woerpel",

year = "2006",

month = "5",

day = "11",

doi = "10.1021/ol060596g",

language = "English (US)",

volume = "8",

pages = "2127--2130",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

AU - Romero, Antonio

AU - Woerpel, Keith

PY - 2006/5/11

Y1 - 2006/5/11

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=33744773513&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33744773513&partnerID=8YFLogxK

U2 - 10.1021/ol060596g

DO - 10.1021/ol060596g

M3 - Article

C2 - 16671798

AN - SCOPUS:33744773513

VL - 8

SP - 2127

EP - 2130

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

Access to Document

10.1021/ol060596g