Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis

被引:2516
作者
Trost, BM [1 ]
Crawley, ML [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/cr020027w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Since the first realization of high enantioselectivity in transition-metal-catalyzed asymmetric allylic alkyllations nearly a decade ago, the use of this process became a vibrant area of study. Recently, both palladium- and molybdenum-catalyzed reactions have achieved dynamic kinetic asymmetric transformations of chiral racemic substrates to enantiopure products, without the 50% yield limitation that was inherent to kinetic resolutions or kinetic asymmetric transformations. The potential of the asymmetic alkylation reaction continues to grow with the development of new ligands, nucleophiles, and processes.
引用
收藏
页码:2921 / 2943
页数:23
相关论文
共 127 条
[1]   MANNOSTATIN-A AND MANNOSTATIN-B - NEW INHIBITORS OF ALPHA-D-MANNOSIDASE, PRODUCED BY STREPTOVERTICILLIUM-VERTICILLUS VAR QUINTUM ME3-AG3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].
AOYAGI, T ;
YAMAMOTO, T ;
KOJIRI, K ;
MORISHIMA, H ;
NAGAI, M ;
HAMADA, M ;
TAKEUCHI, T ;
UMEZAWA, H .
JOURNAL OF ANTIBIOTICS, 1989, 42 (06) :883-889
[2]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[3]   Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease [J].
Bai, DL ;
Tang, XC ;
He, XC .
CURRENT MEDICINAL CHEMISTRY, 2000, 7 (03) :355-374
[4]  
Bergner EJ, 2000, EUR J ORG CHEM, V2000, P419, DOI 10.1002/(SICI)1099-0690(200002)2000:3<419::AID-EJOC419>3.0.CO
[5]  
2-N
[6]   Bis(aminophosphine)-nickel complexes as efficient catalysts for alkylation of allylic acetates with stabilized nucleophiles [J].
Bricout, H ;
Carpentier, JF ;
Mortreux, A .
TETRAHEDRON LETTERS, 1996, 37 (34) :6105-6108
[7]   ALLYLIC ALKYLATION CATALYZED BY PLATINUM COMPLEXES - STRUCTURE AND REACTIVITY OF INTERMEDIATES, AND THE OVERALL STEREOSELECTIVITY [J].
BROWN, JM ;
MACINTYRE, JE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (07) :961-970
[8]   A new approach to (-)-swainsonine by ruthenium-catalyzed ring rearrangement [J].
Buschmann, N ;
Rückert, A ;
Blechert, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4325-4329
[9]  
Dewey SL, 1999, SYNAPSE, V31, P76
[10]  
Dierkes P, 1998, ANGEW CHEM INT EDIT, V37, P3116, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3116::AID-ANIE3116>3.0.CO