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

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posted on 2017-12-22, 00:00 authored by Vadlamuri Veeraswamy, Gaurav Goswami, Satobhisha Mukherjee, Koena Ghosh, Manik Lal Saha, Arunava Sengupta, Manas K. Ghorai
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.

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