Enantioselective protonation of samarium enolates derived from α- heterosubstituted ketones and lactone by SmI2-mediated reduction
SmI2-mediated reductive cleavage of α-heterosubstituents of α-alkyl or α-aryl ketones and lactone gave the corresponding 'thermodynamic samarium enolates'. Enantioselective protonation of the samarium enolates with C2- symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.
Preparation of optically active ketones via enantioface-differentiating protonation of prochiral enolates
Enantioselective protonation of the prochiral lithium enolate (2) of 2-benzylcyclohexanone (3) was developed. Reaction of 2 with methyl (S)-α-hydroxyisocaproate (15) as a chiral proton source afforded (R)-3 in a high optical yield. This reaction is widely applicable to the preparation of various α-substituted optically active ketones.
Matsumoto,Ohta
p. 4729 - 4732
(2007/10/02)
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