Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl alpha, beta-unsaturated ketones: construction of chiral functionalized tetrahydroquinolines

摘要

The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl alpha, beta-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee). (C) 2014 Elsevier Ltd. All rights reserved.