Synthesis of enantiomerically enriched β-amino alcohol derivatives via asymmetric lithiation of O-benzyl carbamates-imine addition using (-)-sparteine complexes

被引:13
作者
Arrasate, S [1 ]
Lete, E [1 ]
Sotomayor, N [1 ]
机构
[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain
关键词
D O I
10.1016/S0957-4166(02)00078-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric lithiation of O-benzyl carbamates-imine addition sequence using sec-butyllithium/(-)-sparteine complexes has been studied. The reactions proceed with high diastereoselectivity, giving the threo beta-amino alcohol derivatives with modest to good e.e. The best enantioinduction was obtained with O-benzyl carbamates bearing methoxy substituents on the aromatic ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:311 / 316
页数:6
相关论文
共 47 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Dynamic thermodynamic resolution: Control of enantioselectivity through diastereomeric equilibration [J].
Beak, P ;
Anderson, DR ;
Curtis, MD ;
Laumer, JM ;
Pippel, DJ ;
Weisenburger, GA .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (10) :715-727
[3]   Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].
Beak, P ;
Basu, A ;
Gallagher, DJ ;
Park, YS ;
Thayumanavan, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560
[4]  
Behrens K, 1998, EUR J ORG CHEM, V1998, P2397
[5]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[6]   CATALYTIC ASYMMETRIC C-C BOND FORMATION - NEW ENOLATOLITHIUM AND ORGANOLITHIUM CHEMISTRY [J].
BERRISFORD, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (02) :178-180
[7]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[8]   GENERATION OF CONFIGURATIONALLY STABLE, ENANTIOENRICHED ALPHA-OXY-ALPHA-METHYLBENZYLLITHIUM - STEREODIVERGENCE OF ITS ELECTROPHILIC SUBSTITUTION [J].
CARSTENS, A ;
HOPPE, D .
TETRAHEDRON, 1994, 50 (20) :6097-6108
[9]   Expanding synthetic utilities of asymmetric dihydroxylation reaction:: Conversion of syn-diols to syn-amino alcohols [J].
Cho, GY ;
Ko, SY .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8745-8747
[10]  
Denmark S. E., 1999, COMPREHENSIVE ASYMME