Cycle-Specific Organocascade Catalysis: Application to Olefin Hydroamination, Hydro-oxidation, and Amino-oxidation, and to Natural Product Synthesis

被引:209
作者
Simmons, Bryon [1 ]
Walji, Abbas M. [1 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
关键词
cascade reactions; enantioselectivity; natural products; organocatalysis; ASYMMETRIC ALPHA-AMINATION; ENAMINE CATALYSIS; DIAMINATION; STRATEGY; DESIGN; ROUTE;
D O I
10.1002/anie.200900220
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
United in effort: The combined application of iminium (Im) and enamine (En) catalysts can effect a range of valuable asymmetric transformations including 1,2-hydroamination, - hydro-oxidation, and -amino-oxidation of olefins (see picture). An enantioselective organocascade catalysis was also applied in the synthesis of a complex natural product. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4349 / 4353
页数:5
相关论文
共 46 条
[1]  
[Anonymous], 2004, ANGEW CHEM
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[4]   TERPENOIDS .74. SESQUITERPENES FROM SOFT CORAL SINULARIA-MAYI [J].
BEECHAN, CM ;
DJERASSI, C ;
EGGERT, H .
TETRAHEDRON, 1978, 34 (16) :2503-2508
[5]   Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].
Brochu, MP ;
Brown, SP ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109
[6]   The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].
Brown, SP ;
Goodwin, NC ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194
[7]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[8]   Organocatalytic asymmetric synthesis of α,α-disubstituted α-amino acids and derivatives [J].
Cabrera, Silvia ;
Reyes, Efraim ;
Aleman, Jose ;
Milelli, Andrea ;
Kobbelgaard, Sara ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (36) :12031-12037
[9]   Enantioselective organocatalytic amine conjugate addition [J].
Chen, Young K. ;
Yoshida, Masanori ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9328-9329
[10]   One-pot multi-component asymmetric cascade reactions catalyzed by soluble star polymers with highly branched non-interpenetrating catalytic cores [J].
Chi, Yonggui ;
Scroggins, Steven T. ;
Frechet, Jean M. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (20) :6322-+