139079-86-0Relevant academic research and scientific papers
Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides
Fujii, Mikio,Fukumura, Motonori,Hori, Yumiko,Hirai, Yasuaki,Akita, Hiroyuki,Nakamura, Kaoru,Toriizuka, Kazuo,Ida, Yoshiteru
, p. 2292 - 2298 (2006)
rac-Hept-1-en-3-ol 4 was subjected to an enantioselective esterification in the presence of Novozyme 435 and vinyl crotonate as the acyl donor to give (3S)-oct-1-en-3-yl crotonate 7 in >99% ee and (3R)-alcohol 4 in 99% ee. The E-value of this enzymatic reaction was found to be >1000. The (S)-crotonic ester 7 was converted by ring-closing metathesis (RCM) using Grubbs' catalyst to give (S)-oct-2-en-4-olide 1 in 96% yield while keeping the high enantiomeric excess.
