Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes.
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.
Liu
Lei
L
Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu 730000, China.
Wang
Rui
R
Kang
Yong-Feng
YF
Chen
Chao
C
Xu
Zhao-Qing
ZQ
Zhou
Yi-Feng
YF
Ni
Ming
M
Cai
Hua-Qing
HQ
Gong
Mao-Zhen
MZ
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry* / Q000378:metabolism; D006841:Hydrocarbons, Aromatic / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D006841:Hydrocarbons, Aromatic; D007659:Ketones; C044736:phenylacetylene; D000535:Aluminum; D000114:Acetylene