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) |
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Pages (from-to) | 2127-2130 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 8 |
Issue number | 10 |
DOIs | |
State | Published - May 11 2006 |
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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 journal › Article
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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 -