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- Title
Regio‐ and Enantioselective Synthesis of 1,2‐Diamines by Formal Hydroamination of Enamines: Scope, Mechanism, and Asymmetric Synthesis of Orthogonally Protected Bis‐Piperazines as a Privileged Scaffold.
- Authors
Mohiti, Maziar; Lu, Yu; He, Hui; Ni, Shao‐Fei; Somfai, Peter
- Abstract
We have previously reported the first formal hydroamination of enamines for the synthesis of chiral 1,2‐diamines. Here, we describe: (i) the discovery, optimization, and substrate expansion of this reaction; (ii) a novel and straightforward protocol for the "click‐type" synthesis of enamines in quantitative yield utilizing sodium sulfate in a dual role as an ancillary and dehydrating agent without the need for workup or purification; (iii) the application of this methodology to the first enantioselective synthesis of orthogonally protected 1,1′‐(1‐(4‐fluorophenyl)ethane‐1,2‐diyl) piperazines, a scaffold for rapid lead optimization in drug discovery; (iv) a computational investigation into the mechanism and rationalization of the enantioselectivities of the reaction.
- Subjects
ENAMINES; ASYMMETRIC synthesis; DRYING agents; HYDROAMINATION; DIAMINES; PIPERAZINE; DRUG discovery; SODIUM sulfate
- Publication
Chemistry - A European Journal, 2024, Vol 30, Issue 16, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202303078