Journal
ORGANIC LETTERS
Volume 18, Issue 24, Pages 6388-6391Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03285
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beta-Aminoacrylates are reactive intermediates that are useful building blocks in synthesis. General methods for their preparation typically afford alpha and beta disubstitution patterns or beta only. Molecules with only alpha-substituents (beta-hydrogen) are much less well-known. A chemoselective reductive tautomerization of alpha-cyanoacetates, using DIBAL-H, has been developed to access these valuable synthons. alpha,beta-Unsaturated cyanoacetates and alpha-cyanoketones can, also, be selectively reduced via this methodology. A series of heterocycles were prepared using these beta-enamino carbonyl compounds.
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