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Synfacts 2011(4): 0445-0445  
DOI: 10.1055/s-0030-1259611
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Vinylogous Aldol Reactions of Furanones and α-Keto Esters

Contributor(s): Benjamin List, Steffen Müller
J. Luo, H. Wang, X. Han, L.-W. Xu, J. Kwiatkowski, K.-W. Huang, Y. Lu*
King Abdullah University of Science and Technology, Kingdom of Saudi Arabia, National University of Singapore, Singapore and Hangzhou Normal University, P. R. of China
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

The organocatalytic direct asymmetric vinylogous aldol reaction between furan­ones and α-keto esters is reported. The trypto­phan-derived bifunctional catalyst 1, consisting of a tertiary amine and a thiourea moiety, delivered the desired addition products, bearing a quaternary stereocenter, in good to high yields and stereoselectivities. The authors found that the dihalogenation of the furanone improved reactivity since the nonhalogenated analogues led to increased reaction times. A plausible transition state is provided and possible derivatizations of the products are shown.