New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction

被引:1345
作者
Ahrendt, KA [1 ]
Borths, CJ [1 ]
MacMillan, DWC [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja000092s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:4243 / 4244
页数:2
相关论文
共 29 条
[1]   STEREOCHEMISTRY .59. NEW INSIGHTS INTO THE MECHANISM OF THE PROLINE-CATALYZED ASYMMETRIC ROBINSON CYCLIZATION - STRUCTURE OF 2 INTERMEDIATES - ASYMMETRIC DEHYDRATION [J].
AGAMI, C ;
MEYNIER, F ;
PUCHOT, C ;
GUILHEM, J ;
PASCARD, C .
TETRAHEDRON, 1984, 40 (06) :1031-1038
[2]  
[Anonymous], COMPREHENSIVE ASYMME
[3]   Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2'-binaphthol and a vaulted 3,3'-biphenanthrol (VAPOL) [J].
Bao, JM ;
Wulff, WD ;
Dominy, JB ;
Fumo, MJ ;
Grant, EB ;
Rob, AC ;
Whitcomb, MC ;
Yeung, SM ;
Ostrander, RL ;
Rheingold, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3392-3405
[4]   SYNTHESIS AND CYCLOADDITION REACTIONS OF ACETYLENIC IMINIUM COMPOUNDS [J].
BAUM, JS ;
VIEHE, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :183-187
[5]   1ST APPLICATION OF ATTRACTIVE INTRAMOLECULAR INTERACTIONS TO THE DESIGN OF CHIRAL CATALYSTS FOR HIGHLY ENANTIOSELECTIVE DIELS-ALDER REACTIONS [J].
COREY, EJ ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8966-8967
[6]   DEMONSTRATION OF THE SYNTHETIC POWER OF OXAZABOROLIDINE-CATALYZED ENANTIOSELECTIVE DIELS-ALDER REACTIONS BY VERY EFFICIENT ROUTES TO CASSIOL AND GIBBERELLIC-ACID [J].
COREY, EJ ;
GUZMANPEREZ, A ;
LOH, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3611-3612
[7]   Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt [J].
Corey, EJ ;
Zhang, FY .
ORGANIC LETTERS, 1999, 1 (08) :1287-1290
[8]   Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].
Corey, EJ ;
Bo, YX ;
Busch-Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001
[9]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[10]  
Denmark SE, 1999, SYNLETT, P847