Asymmetric cooperative catalysis in a three-component reaction: mechanism and origin of enantio- and diastereoselectivities

Kisan, Hemanta K. ; Sunoj, Raghavan B. (2016) Asymmetric cooperative catalysis in a three-component reaction: mechanism and origin of enantio- and diastereoselectivities Organic Letters, 18 (15). pp. 3746-3749. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b...

Related URL: http://dx.doi.org/10.1021/acs.orglett.6b01765

Abstract

Mechanistic insights gained through Density functional Theory (DFT M06 and B3LYP) computations on a three-component cooperative asymmetric catalytic reaction between a diazo ester, a carbamate and an imine, catalyzed by dirhodium acetate and chiral phosphoric acid (Bronsted acid), are presented. The addition of the dirhodium-bound enol to the imine yielding an α,β-diamino ester is energetically more preferred over a potentially competitive protonation of the same enol leading to an α-amino ester.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:109686
Deposited On:02 Aug 2017 11:45
Last Modified:02 Aug 2017 11:45

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