4,4′-disubstituted BINAPs for highly enantioselective Ru-catalyzed asymmetric hydrogenation of ketones

被引：64
|
作者：
Hu, AG [1 ]
Ngo, HL [1 ]
Lin, WB [1 ]
机构：
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 17期
关键词：
D O I：
10.1021/ol048993j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A family of tunable precatalysts Ru(4,4'-BINAP)(chiral diamine)Cl-2 was synthesized and used for highly enantioselective hydrogenation of aromatic ketones. This result differs from previous chiral diphosphines that rely on the bis(xylyl)phosphino groups to control enantioselectivity. An X-ray structural study reveals that the bulky substituents on the 4,4'-positions of BINAP can effectively create a suitable chiral pocket in the transition state and thus provide a new mechanism for the enantiocontrol in such a remarkable asymmetric catalytic process.
引用
收藏
页码：2937 / 2940
页数：4
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