Domino Multicomponent Michael-Michael-Aldol Reactions under Phase-Transfer Catalysis: Diastereoselective Synthesis of Pentasubstituted Cyclohexanes

abstract

A simple, efficient, and environmental friendly domino multicomponent reaction to construct new cyclohexane derivatives with five new stereocenters, one of them quaternary, under phase-transfer catalysis is reported. This novel one-pot reaction allows the transformation of very simple starting materials into pentasubstituted cyclohexane derivatives bearing hydroxy, nitro, and ketone moieties and involving the formation of three new C-C bonds. All compounds have been formed in a completely diastereoselective way and have been isolated in high yields.

keywords

HIGHLY STEREOSELECTIVE-SYNTHESIS; CASCADE REACTIONS; 4 STEREOCENTERS; ALPHA,BETA-UNSATURATED ALDEHYDES; ASYMMETRIC-SYNTHESIS

subject category

Chemistry

authors

Resende, DISP; Oliva, CG; Silva, AMS; Paz, FAA; Cavaleiro, JAS

our authors

acknowledgements

Thanks are due to the University of Aveiro, to Fundacao para a Ciencia e a Tecnologia' and FEDER for funding the Organic Chemistry Research Unit and for the financial support towards the purchase of the single-crystal diffractometer.

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