Journal of Organic Chemistry p. 1707 - 1712 (1992)
Update date:2022-08-04
Topics:
Nemoto, Hideo
Ishibashi, Hiroki
Nagamochi, Masatoshi
Fukumoto, Keiichiro
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).
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