Enantioselective Synthesis of Dihydrospiro[indoline-3,4'-pyrano[2,3-c]pyrazole] Derivatives via Michael/Hemiketalization Reaction.

Org Lett

Chemical Biology Laboratory, Department of Biotechnology, Bhupat and Jyoti Mehta School of Biosciences, Indian Institute of Technology Madras, Chennai 600036, India.

Published: March 2016

A new bifunctional squaramide organocatalyst derived from L-proline mediated the first enantioselective synthesis of dihydrospiro[indoline-3,4'-pyrano[2,3-c]pyrazole] derivatives in excellent enantioselectivity by reacting pyrazolones with isatylidine β,γ-unsaturated α-ketoester. This new catalyst outperformed widely used thioureas and squaramides in inducing enantioselectivity.

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http://dx.doi.org/10.1021/acs.orglett.6b00287DOI Listing

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