- Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers
-
The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58-90% de). In all cases, small amounts (2-symmetric dl-3,4-diaryladipic acids and trans-3,4-diarylcyclopentanones. The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, prepared from (1R)-(+)-camphor, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.
- Kise, Naoki,Iitaka, Shumei,Iwasaki, Keisuke,Ueda, Nasuo
-
p. 8305 - 8315
(2007/10/03)
-