An NH2CN-promoted convergent integration of three self-sorting domino sequences is described for the construction of 6-iodo-3-methylthioimidazo[1,2-a]pyridines from aryl methyl ketones and 2-aminopyridines. This strategy allows the construction of an imidazo[1,2-a]pyridine ring along with methylthiolation at C-3 and iodination at C-6. Preliminary mechanistic studies indicate that this process t...

[Chemical reaction: see text] We report the first examples of a Michael-Stork enamine addition to allenyl esters and ketones. Studies reveal that 2 equivalents of enamine are required for optimal yields. In the case of an allenyl methyl ketone, cyclopentyl enamine addition led to 8-oxobicyclo[3.2.1]octane formation, providing evidence for the in situ formation of an enamine intermediate followi...

Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0-5.0 mol % of chiral NHC-Cu complexes, B2(pin)2, and t-BuOH proceed to afford alkenyl-B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What's mo...

A highly efficient method for the construction of 3a,6a-dihydrofuro[2,3-b]furan derivatives has been developed via a novel bicyclization, which is very valuable for the synthesis of fused furofuran compounds since it is time-saving and catalyst-free. Based on the bicyclization, a coupled domino strategy has been developed to directly construct 3a,6a-dihydrofuro[2,3-b]furan derivatives from meth...

The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions an...

This paper describes an operationally simple deracemization process of aldehydes and ketones. This new crystallization-induced dynamic resolution (CIDR) protocol allows for nearly complete conversion of the racemic mixture into one enantiomer. Crystallization of imines derived from racemic ketones or aldehydes 1 and trans-(1R,2R)-1-amino-6-nitroindan-2-ol (2) afforded diastereomerically pure, c...