CATALYTIC ASYMMETRIC ALLYLATION USING A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS-ACID CATALYST

被引:166
作者
ISHIHARA, K [1 ]
MOURI, M [1 ]
GAO, QZ [1 ]
MARUYAMA, T [1 ]
FURUTA, K [1 ]
YAMAMOTO, H [1 ]
机构
[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA 46401,JAPAN
关键词
D O I
10.1021/ja00077a054
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.
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页码:11490 / 11495
页数:6
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