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

被引：36

作者：

Romero, A ^{[1
]}

Woerpel, KA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 10期

关键词：

D O I：

10.1021/ol060596g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of gamma-lactams by the [3+2] annulation of alpha-siloxy allylic silanes with N-chlorosulfonyl isocyanate (CISO2NCO) was developed. The use of these allylic silanes allowed for further diastereoselective substitution of the resultant N,O-acetal to give highly substituted gamma-lactams. Oxidation of the silyl group afforded access to complex beta-hydroxy-gamma-lactams.

引用

页码：2127 / 2130

页数：4

共 50 条

[1] Stereoselective synthesis of substituted γ-butyrolactones by the [3+2] annulation of allylic silanes with chlorosulfonyl isocyanate:: Enantioselective total synthesis of (+)-blastmycinone
Peng, ZH
Woerpel, KA
[J]. ORGANIC LETTERS, 2001, 3 (05) : 675 - 678
[2] Formal synthesis of (±)-peduncularine:: Use of the [3+2] annulation of allylic silanes and chlorosulfonyl isocyanate
Roberson, CW
Woerpel, KA
[J]. ORGANIC LETTERS, 2000, 2 (05) : 621 - 623
[3] The [3+2] annulation of allylsilanes and chlorosulfonyl isocyanate: Stereoselective synthesis of 2-pyrrolidinones
Roberson, CW
Woerpel, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1434 - 1435
[4] The [3+2] annulation of allylsilanes and chlorosulfonyl isocyanate: Stereoselective synthesis of 2-pyrrolidinones.
Roberson, CW
Woerpel, KA
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U210 - U210
[5] [3+2] cycloaddition of allylic silane with N-chlorosulfonyl isocyanate
Isaka, M
Williard, PG
Nakamura, E
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (09) : 2115 - 2116
[6] Total synthesis of asimicin via highly stereoselective [3+2] annulation reactions of substituted allylsilanes
Tinsley, JM
Roush, WR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) : 10818 - 10819
[7] Total synthesis of (±)-peduncularine:: Application of the formal [3+2] annulation of cyclohexadienyl silane and chlorosulfonyl isocyanate.
Woerpel, KA
Roberson, CW
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U99 - U99
[8] Benzhydryldimethylsilyl allylic silanes: Syntheses and applications to [3+2] annulation reactions
Peng, ZH
Woerpel, KA
[J]. ORGANIC LETTERS, 2000, 2 (10) : 1379 - 1381
[9] Stereoselective synthesis of heterocycles by annulation reactions of allylic silanes.
Woerpel, KA
Peng, ZH
Roberson, CW
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U181 - U182
[10] [3+2] Annulation of allylic silanes in acyclic stereocontrol:: Total synthesis of (9S)-dihydroerythronolide A
Peng, ZH
Woerpel, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) : 6018 - 6019

← 1 2 3 4 5 →