Lithium binaphtholate-catalyzed enantioselective enyne addition to ketones: access to enynylated tertiary alcohols.
A new catalytic enantioselective enyne addition to ketones has been developed. In the presence of chiral lithium binaphtholate, the addition reaction proceeded smoothly to produce a series of enynylated tertiary alcohols in up to 96% yield and 94% enantiomeric excess. Convenient transformation of the adduct via Pauson-Khand cycloaddition reaction afforded the bicyclic product without detectable loss of enantioselectivity. Furthermore, catalytic asymmetric enyne addition to trifluoromethylketone was applied in the synthesis of the Efavirenz analogue.
Department of Chemistry, Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University , and Collaborative Innovation Centre of Chemical Science and Engineering (Tianjin) , Tianjin 300072, China.
Hua
H
Cai
Jing
J
Nie
Yan
Y
Zheng
Jun-An
JA
Ma
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D007659:Ketones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000480:Alkynes; D007659:Ketones; D009281:Naphthalenes; D008094:Lithium