Dramatic change of regioselectivity in the addition of silylated organolithium reagents with oxazolidines induced by the presence of a titanium salt

被引:10
作者
Agami, C [1 ]
Comesse, S [1 ]
Kadouri-Puchot, C [1 ]
机构
[1] Univ Paris 06, UMR 7611, Lab Synth Asymetr, F-75005 Paris, France
关键词
D O I
10.1016/S0040-4039(00)00947-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diastereoselective reactions between oxazolidines and organolithium reagents afford beta-amino alcohols having chiral vinyl and alkynylsilane moieties. A meaningful change of regioselectivity, from the alpha- to the gamma-position, occurred when those reactions were performed in the presence of titanium isopropoxide, since allyl and allenylsilane derivatives were thus produced. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6059 / 6062
页数:4
相关论文
共 28 条
[1]  
Agami C, 1999, SYNLETT, P1094
[2]   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
[3]  
Allin SM, 1998, SYNLETT, P1117
[4]  
AMOUROUX R, 1978, TETRAHEDRON LETT, P4453
[5]   NEW BETA-ACYLCARBANION EQUIVALENT BASED ON ALLYLTRIMETHYLSILANE CHEMISTRY [J].
AYALONCHASS, D ;
EHLINGER, E ;
MAGNUS, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (21) :772-773
[6]   Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].
Bloch, R .
CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438
[7]  
CHAN TH, 1979, SYNTHESIS-STUTTGART, P761
[8]   SYNTHESES THAT BEGIN WITH SILYLATED ALLYLIC CARBANIONS .1. CARBANIONS DERIVED FROM MONO-ALLYL-SILANES [J].
CORRIU, RJP ;
MASSE, J ;
SAMATE, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (01) :71-80
[9]   Asymmetric synthesis of diarylmethylamines: preparation of selective opioid delta receptor ligands [J].
Delorme, D ;
Berthelette, C ;
Lavoie, R ;
Roberts, E .
TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3963-3966
[10]   SILICON IN SYNTHESIS .10. THE (TRIMETHYLSILYL)ALLYL ANION - A BETA-ACYL ANION EQUIVALENT FOR THE CONVERSION OF ALDEHYDES AND KETONES INTO GAMMA-LACTONES [J].
EHLINGER, E ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (15) :5004-5011