‘On water’ direct vinylogous Henry (nitroaldol) reactions of 3,5-dimethyl-4-nitroisoxazole with aldehydes and trifluoromethyl ketones

Abstract An efficient ‘on water’-promoted direct catalytic vinylogous addition of 3,5-dimethyl-4-nitroisoxazole to aldehydes and trifluoromethyl ketones was described, giving Henry (nitroaldol) adducts in excellent yields. The trifluoromethyl tertiary alcohol product could be transformed to the corresponding styrene derivative, which was demonstrated as a new type of Michael acceptor in the vinylogous 1,6-Michael addition with nitromethane.