10.1021/jo5005839.s003
Hua Cai
Hua
Cai
Jing Nie
Jing
Nie
Yan Zheng
Yan
Zheng
Jun-An Ma
Jun-An
Ma
Lithium Binaphtholate-Catalyzed
Enantioselective Enyne
Addition to Ketones: Access to Enynylated Tertiary Alcohols
American Chemical Society
2014
bicyclic product
addition reaction
Efavirenz analogue
chiral lithium binaphtholate
Convenient transformation
enyne addition
Enynylated Tertiary AlcoholsA
enantioselective enyne addition
2014-06-20 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Lithium_Binaphtholate_Catalyzed_Enantioselective_Enyne_Addition_to_Ketones_Access_to_Enynylated_Tertiary_Alcohols/2280892
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.