Enantioselective Intramolecular Dearomative Lactonization of Naphthols Catalyzed by Planar Chiral Iodoarene

Abstract

A series of planar chiral iodoarenes based on [2.2]paracyclophane was synthesized. An efficient asymmetric intramolecular oxidative lactonization of naphthols enabled by a combination of these chiral iodoarenes and mCPBA as oxidant is reported. This reaction proceeds under mild conditions, allowing the formation of spirolactones bearing a tetrasubstituted stereocenter in moderate yields and good enantioselectivity.

Key words

hypervalent iodine catalysis - [2.2]paracyclophane - planar chirality - asymmetric dearomatization - oxidative lactonization

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