Enantioselective reduction of α,β-unsaturated acylsilanes by chiral lithium amides

被引:48
作者
Takeda, K [1 ]
Ohnishi, Y [1 ]
Koizumi, T [1 ]
机构
[1] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan
关键词
D O I
10.1021/ol990574c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of beta-substituted acryloylsilanes I with lithium amides II affords a-silyl allylic alcohols III in high enantiomeric excess (>99%) via formal hydride transfer from the chiral lithium amide.
引用
收藏
页码:237 / 239
页数:3
相关论文
共 25 条
[1]   THE CONVERSION OF ACYL SILANES INTO CHIRAL SECONDARY ALCOHOLS [J].
BUYNAK, JD ;
STRICKLAND, JB ;
HURD, T ;
PHAN, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :89-90
[2]   THERMAL REARRANGEMENTS OF ALPHA-(ACYLOXY)SILANES .2. FORMATION OF CHIRAL PRECURSORS AND MIGRATORY PREFERENCE OF SILICON-BASED GROUPS [J].
BUYNAK, JD ;
STRICKLAND, JB ;
LAMB, GW ;
KHASNIS, D ;
MODI, S ;
WILLIAMS, D ;
ZHANG, HM .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7076-7083
[3]   ASYMMETRIC REDUCTIONS .55. ASYMMETRIC REDUCTION OF DIARYL KETONES WITH "(S)-(+)-1-LITHIO-2-METHYLPIPERIDINE [J].
CERVINKA, O ;
DUDEK, V ;
SCHOLZOVA, I .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1978, 43 (04) :1091-1092
[4]  
CHO SG, 1996, J MOL STRUC-THEOCHEM, V364, P59
[5]  
Cirillo P. F., 1992, ORG PREP P INT, V24, P553
[6]   STUDIES DIRECTED TOWARD THE SYNTHESIS OF (+)-SESBANIMIDE-A - CONSTRUCTION OF THE AB-RING SYSTEM (A FORMAL TOTAL SYNTHESIS) [J].
CIRILLO, PF ;
PANEK, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3055-3063
[7]   ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].
COX, PJ ;
SIMPKINS, NS .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26
[8]  
HERRMANN JL, 1973, TETRAHEDRON LETT, P2433
[9]   REDUCTIONS OF ALPHA-SUBSTITUTED KETONES BY LITHIUM DIISOPROPYLAMIDE [J].
KOWALSKI, C ;
CREARY, X ;
ROLLIN, AJ ;
BURKE, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2601-2608
[10]   ARYL-SUBSTITUTED CYCLIC HOMOALDOL PRODUCTS DERIVED FROM (ALPHA-ALKOXYBENZYL)TRIMETHYLSILANES [J].
LINDERMAN, RJ ;
GHANNAM, A ;
BADEJO, I .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5213-5216