Synfacts 2011(6): 0680-0680  
DOI: 10.1055/s-0030-1260420
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Vinylogous Michael Addition of Furanones to Nitroolefines

Contributor(s): Benjamin List, Steffen Müller
M. Terada*, K. Ando
Tohoku University, Sendai, Japan
Further Information

Publication History

Publication Date:
19 May 2011 (online)

Significance

Terada and Ando report the direct asymmetric vinylogous Michael addition of 3-(tert-butylthio)furan-2(5H)-one (1) to nitroolefins 2, catalyzed by the chiral guanidine base 3 (5 mol%). The corresponding γ-butenolide products were obtained in good yields and good enantio- and ­diastereoselectivities for a variety of different nitro­olefins. The tert-butyl substituent at the sulfur atom of 1 was found to be crucial for the observed selectivities. Some possible derivatizations of the Michael adducts are also presented.