期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 17, 页码 7570-7574出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja303022d
关键词
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资金
- University of Bristol
- EPSRC
Enantioenriched secondary allylic carbamates have been deprotonated with sBuLi and reacted with boronic esters. In contrast to other electrophiles, high alpha-selectivity was observed and the boronate complexes were formed with almost complete retention of stereochemistry. The boronate complexes underwent a stereospecific 1,2-migration leading to tertiary allylic boronic esters with high er (>98:2). The scope of the reaction has been explored and found to embrace a broad range of both allylic carbamates and boronic esters. The methodology has been applied to an eight-step, stereoselective synthesis of each of the diastereoisomers of C30 botryococcene.
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