Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles.

Chemistry

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.

Published: March 2018

Asymmetric cascade double Michael additions to construct 2'-substituted 3,3'-spirooxindoles by using a chiral guanidine organocatalyst has been developed. A series of spirooxindole derivatives containing dihydrofuran or pyrrolidine subunits were obtained with good to excellent diastereo- and enantioselectivities. The method showed great tolerance of a number of aromatic and aliphatic alkynones. The strategy gave access to the asymmetric synthesis of (-)-salacin for the first time.

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http://dx.doi.org/10.1002/chem.201800043DOI Listing

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