139240-50-9Relevant academic research and scientific papers
Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation
Wang, Bin,Shen, Yu-Mei,Shi, Yian
, p. 9519 - 9521 (2007/10/03)
(Chemical Equation Presented) This paper describes an enantioselective synthesis of γ-butyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as oxidant via a sequential asymmetric epoxidation of benzylidenecyclopropanes, ring expansion, and Baeyer-Villiger oxidation. Up to 91% ee was obtained. Optically active cyclobutanones can also be obtained by suppressing the Baeyer-Villiger oxidation with use of more ketone catalyst and less Oxone.
A Concise and Enantioselective Approach to Cyclobutanones by Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols. An Enantiocontrolled Synthesis of (+)- and (-)-α-Cuparenones
Nemoto, Hideo,Ishibashi, Hiroki,Nagamochi, Masatoshi,Fukumoto, Keiichiro
, p. 1707 - 1712 (2007/10/02)
A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess.These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons.Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-cuparenones (11).
