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Gold-catalyzed oxidative ring expansions and ring cleavages of alkynylcyclopropanes by intermolecular reactions oxidized by diphenylsulfoxide
Journal article   Peer reviewed

Gold-catalyzed oxidative ring expansions and ring cleavages of alkynylcyclopropanes by intermolecular reactions oxidized by diphenylsulfoxide

Chia-Wen Li, Kamalkishore Pati, Guan-You Lin, Shariar Md. Abu Sohel, Hsiao-Hua Hung and Rai-Shung Liu
Angewandte Chemie - International Edition, Vol.49(51), pp.9891-9894
17/12/2010

Abstract

cyclopropanes diphenylsulfoxides gold oxidation ring-expansion
A golden opportunity: A novel gold-catalyzed oxidative ring-expansion of unactivated cyclopropylalkynes using Ph 2 SO has been developed (see scheme). For substrates bearing a donor group at the cyclopropane ring, preliminary results reveal a distinct cleavage of the cyclopropane unit; such a ring cleavage is further applicable to the synthesis of 2H-pyrans. L=P(tBu) 2 (o-biphenyl), Tf=triflate. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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