Enantioselective Trapping of Oxonium Ylides by 3-Hydroxyisoindolinones via a Formal S1 Pathway for Construction of Contiguous Quaternary Stereocenters.

Org Lett

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.

Published: February 2018

An enantioselective Rh(II)/chiral phosphoric acid co-catalyzed three-component reaction via trapping of oxonium ylides with 3-hydroxyisoindolinones by a formal S1 pathway is described. This reaction allows for the efficient synthesis of isoindolinone derivatives with two contiguous quaternary stereogenic centers in high yields (up to 93%) with excellent enantioselectivities and moderate diastereoselectivities under mild reaction conditions.

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http://dx.doi.org/10.1021/acs.orglett.7b03916DOI Listing

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