Regioselectivity-reversed asymmetric aldol reaction of 1,3-dicarbonyl compounds.

Chemistry

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang Province 325035, PR China.

Published: September 2012

Reverse regioselectivity: The first catalytic asymmetric C-1 functionalization of 1,3-dicarbonyl compounds by an aldol reaction is described, which regioselectively affords 6-hydroxyhexane-2,4-dione derivatives as the only product with high optical purity of up to 93 % ee. Furthermore, this method provides a facile access to enantioenriched oxygen-containing spirooxindoles and spirobutyrolactones from simple commercial available starting materials (see scheme).

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http://dx.doi.org/10.1002/chem.201201874DOI Listing

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