1006879-10-2Relevant articles and documents
Biotransformations of racemic 2,3-allenenitriles in biphasic systems: Synthesis and transformations of enantioenriched axially chiral 2,3-allenoic acids and their derivatives
Ao, Yu-Fei,Wang, De-Xian,Zhao, Liang,Wang, Mei-Xiang
, p. 3103 - 3110 (2014/05/06)
Catalyzed by Rhodococcus erythropolis AJ270 whole cells in an aqueous phosphate buffer-n-hexane biphasic system, racemic axially chiral 2,3-allenenitriles underwent hydrolysis to afford enantioenriched (aR)-2,3-allenamides and (aS)-2,3-allenoic acids with
Synthesis of 1,4-enamino ketones by [3,3]-rearrangements of dialkenylhydroxylamines
Pecak, Wiktoria H.,Son, Jongwoo,Burnstine, Amy J.,Anderson, Laura L.
supporting information, p. 3440 - 3443 (2014/07/21)
The synthesis of 1,4-enamino ketones has been achieved through the [3,3]-rearrangement of dialkenylhydroxylamines generated from the addition of N-alkenylnitrones to electron-deficient allenes. The mild conditions required for this reaction, and the simultaneous installation of a fluorenyl imine N-protecting group as a consequence of the rearrangement, avoid spontaneous cyclization of the 1,4-enamino ketones to form the corresponding pyrroles and allow for the isolation and controlled divergent functionalization of these reactive intermediates. The optimization, scope, and tolerance of the new method are discussed with demonstrations of the utility of the products for the synthesis of pyrroles, 1,4-diones, and furans.