Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes

被引:69
作者
Liu, L
Wang, R [1 ]
Kang, YF
Chen, C
Xu, ZQ
Zhou, YF
Ni, M
Cai, HQ
Gong, MZ
机构
[1] Lanzhou Univ, Dept Biochem & Mol Biol, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
关键词
D O I
10.1021/jo0483522
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols.
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页码:1084 / 1086
页数:3
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