A highly stereoselective TMSOTf-mediated catalytic carbocupration of alkynoates

被引:38
作者
Mueller, Amanda J. [1 ]
Jennings, Michael P. [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
关键词
D O I
10.1021/ol702546w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereoselectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.
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页码:5327 / 5329
页数:3
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