Highly stereoselective [4+3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles. An approach to parvineostemonine

被引：62
作者：
Antoline, Jennifer E.
Hsung, Richard P.
Huang, Jian
Song, Zhenlei
Li, Gang
机构：
[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 07期
关键词：
D O I：
10.1021/ol070103n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly stereoselective [4 + 3] cycloaddition of N-substituted pyrroles with allenamide-derived nitrogen-stabilized chiral oxyallyl cations is described here. This method provides an approach for constructing tropinone alkaloids.
引用
收藏
页码：1275 / 1278
页数：4
相关论文
共 72 条
[41]  
Krause N., 2004, MODERN ALLENE CHEM, V2
[42]  
Krause N., 2004, MODERN ALLENE CHEM, V1
[43]  
Lautens M., 1997, ADV CYCLOAD, V4, P1
[44]   A new approach to phorbol by [4+3] oxyallyl cycloaddition and intramolecular Heck reaction [J].
Lee, KH ;
Cha, JK .
ORGANIC LETTERS, 1999, 1 (03) :523-525
[45]   Diastereoselective [4+3] cycloadditions of enantiopure nitrogen-stabilized oxyallyl cations [J].
MaGee, David I. ;
Godineau, Edouard ;
Thornton, Paul D. ;
Walters, Michael A. ;
Sponholtz, Deborah J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3667-3680
[46]   Applications of vinylogous Mannich reactions. Concise enantiospecific total syntheses of (+)-croomine [J].
Martin, SF ;
Barr, KJ ;
Smith, DW ;
Bur, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (30) :6990-6997
[47]   Highly regio- and stereoselective [3+2] cyclopentanone annulation using a 3-(alkylthio)-2-siloxyallyl cationic species [J].
Masuya, K ;
Domon, K ;
Tanino, K ;
Kuwajima, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1724-1731
[48]   Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis [J].
McReynolds, MD ;
Dougherty, JM ;
Hanson, PR .
CHEMICAL REVIEWS, 2004, 104 (05) :2239-2258
[49]   Asymmetry induction on the [4C(4π)+3C(2π)] cycloaddition reaction of C2-functionalized furans:: influence of the chiral auxiliary nature [J].
Montaña, AM ;
Grima, PM .
TETRAHEDRON, 2002, 58 (24) :4769-4786
[50]   On the inherent instability of α-amino α′-fluoro ketones.: Evidence for their transformation to reactive oxyvinyliminium ion intermediates [J].
Myers, AG ;
Barbay, JK .
ORGANIC LETTERS, 2001, 3 (03) :425-428
12345678