Asymmetric intermolecular C-H functionalization of benzyl silyl ethers mediated by chiral auxiliary-based aryldiazoacetates and chiral dirhodium catalysts

被引:41
作者
Davies, HML [1 ]
Hedley, SJ [1 ]
Bohall, BR [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词
D O I
10.1021/jo051747g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H functionalization of benzyl silyl ethers by means of rhodium-catalyzed insertions of aryldiazoacetates can be achieved in a highly diastereoselective and enantioselective manner by judicious choice of chiral catalyst or auxiliary. The dirhodium tetraprolinates such as Rh-2((S)-DOSP)(4) have been widely successful as chiral catalysts in the C-H functionalization chemistry of aryldiazoacetates, but give poor enantioselectivity in the reactions of aryldiazoacetates with benzyl silyl ether derivatives. The use of (S)-lactate as a chiral auxiliary resulted in C-H functionalization with moderately high diastereoselectivity (79-88% de) and enantioselectivity (68-85% ee). The best results (91-95% de, 95-98% ee), however, were achieved using Hashimoto's Rh-2((S)-PTTL)(4) catalyst.
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页码:10737 / 10742
页数:6
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