2985-33-3Relevant articles and documents
Aspidosperma Alkaloids via Cyclization of Secodine Intermediate: Synthesis of (+/-)-3-Oxovincadifformine Ethyl Ester
Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni,Passarella, Daniele,Silvani, Alessandra
, p. 6941 - 6954 (1994)
(+/-)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular cycloaddition of the 3-oxosecodine 13 first prepared in turn from the enamide 10 by dehydrogenation with benzeneseleninic anhydride.An insight into the conversion of 10 into 13 was gained, resulting in the suggestion of a plausible mechanistic pathway.
Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides
Porey, Arka,Mondal, Bhaskar Deb,Guin, Joyram
supporting information, p. 8786 - 8791 (2021/03/17)
Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.
Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene
Santra, Surojit,Maji, Ujjwal,Guin, Joyram
supporting information, p. 468 - 473 (2020/02/04)
Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.