Remote asymmetric induction in reactions of 5-alkoxyalk-2-enylsilanes and aldehydes promoted by tin(IV) chloride

被引:11
作者
Brain, CT [1 ]
Thomas, EJ [1 ]
机构
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
关键词
D O I
10.1016/S0040-4039(97)00358-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Following observations on remote asymmetric induction using allylstannanes, 5-benzyloxy-4-methylpent-2-enylsilanes are also found to react with aldehydes with modest levels of 1,5-induction after treatment with tin(IV) chloride. Transmetallation to give intermediate allyltin trihalides may be involved. (C) 1997 Elsevier Science Ltd.
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收藏
页码:2387 / 2390
页数:4
相关论文
共 10 条
[1]   THE USE OF METALLOIDS (-SIME3, -SNR3) AS PROTECTED CARBANIONS - SELECTIVE ACTIVATION AND NEW CYCLIZATION PROCESSES [J].
ANDERSEN, NH ;
MCCRAE, DA ;
GROTJAHN, DB ;
GABHE, SY ;
THEODORE, LJ ;
IPPOLITO, RM ;
SARKAR, TK .
TETRAHEDRON, 1981, 37 (23) :4069-4079
[2]  
CAREY JS, 1992, SYNLETT, P585
[3]  
CRITCH D, 1996, J ORG CHEM, V61, P7200
[4]   Stille couplings with fluorous tin reactants: Attractive features for preparative organic synthesis and liquid-phase combinatorial synthesis [J].
Curran, DP ;
Hoshino, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6480-6481
[5]  
FLEMING I, 1979, SYNTHESIS-STUTTGART, P446
[6]   OBSERVATIONS ON VARIOUS SILYL-CUPRATE REAGENTS [J].
FLEMING, I ;
NEWTON, TW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08) :1805-1808
[7]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[8]  
HOBSON LJ, UNPUB
[9]   PRACTICAL SYNTHESES OF ALLYLSILANES FROM 1-BENZENESULFONYL-2-TRIMETHYLSILYLETHANE [J].
HSIAO, CN ;
SHECHTER, H .
TETRAHEDRON LETTERS, 1982, 23 (19) :1963-1966
[10]  
THOMAS EJ, 1994, CHEMTRACTS ORG CHEM, P207