Memory of Chirality Concept in Asymmetric Intermolecular Michael Addition of α-Amino Ester Enolates to Enones and Nitroalkenes

Veeraswamy, Vadlamuri ; Goswami, Gaurav ; Mukherjee, Satobhisha ; Ghosh, Koena ; Saha, Manik Lal ; Sengupta, Arunava ; Ghorai, Manas K. (2018) Memory of Chirality Concept in Asymmetric Intermolecular Michael Addition of α-Amino Ester Enolates to Enones and Nitroalkenes The Journal of Organic Chemistry, 83 (3). pp. 1106-1115. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.7b02315

Related URL: http://dx.doi.org/10.1021/acs.joc.7b02315

Abstract

A highly stereoselective asymmetric intermolecular conjugate addition of α-amino ester derivatives to cyclic enones via the memory of chirality (MOC) concept in high yields with excellent diastereo- and enantioselectivity (dr >99:1, up to 99% ee) is reported. The applicability and the generality of the strategy was demonstrated by its further exploration to acyclic α,β-unsaturated ketone and aromatic nitroalkenes, resulting in the formation of δ-keto-α-amino ester derivative and γ-nitro-α-amino ester derivatives, respectively, with excellent ee and dr.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117089
Deposited On:15 Apr 2021 07:43
Last Modified:15 Apr 2021 07:43

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