25347-44-8Relevant articles and documents
Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers
Kise, Naoki,Iitaka, Shumei,Iwasaki, Keisuke,Ueda, Nasuo
, p. 8305 - 8315 (2007/10/03)
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.
Reaction of α-Substituted β-Bromostyrenes with Dicarbonyldicyanonickelate(0) Anion in Alkaline Medium under Carbon Monoxide
Miura, Masahiro,Shimoura, Nobuhiro,Nomura, Masakatsu
, p. 1993 - 1996 (2007/10/02)
The reactions of (E)- and (Z)-β-bromostyrene (1a) with dicarbonyldicyanonickelate(0) anion generated in situ in the presence of sodium or calcium hydroxide under carbon monoxide gave a carbonylated product mixture of (E)-cinnamic acid , 3,4-diphenylhexanedioic acid (4), and 3-phenylpropionic acid (5).In contrast, in the reactions of α-methyl- and phenyl-β-bromostyrenes (1b and c) the corresponding nitriles (3b and c) were formed, together with the carboxylic acids (2b and c).