Ghorai, Manas K. ; Ghosh, Koena ; Yadav, A. K. ; Nanaji, Y. ; Halder, Sandipan ; Sayyad, Masthanvali (2013) Memory of Chirality (MOC) Concept in Imino-Aldol Reaction: Enantioselective Synthesis of α,β-Diamino Esters and Aziridines The Journal of Organic Chemistry, 78 (6). pp. 2311-2326. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo302018a
Related URL: http://dx.doi.org/10.1021/jo302018a
Abstract
A simple strategy for the synthesis of chiral α,β-diamino- and α-amino,β-hydroxy ester derivatives in high yields with moderate to high ee has been developed via asymmetric imino-aldol and aldol reactions, respectively, starting from protected aminoesters employing memory of chirality concept for chiral induction. This strategy has been extended for the enantioselective synthesis of aziridines (ee up to 92%). The absolute configuration of the imino-aldol adducts has been determined. The stereochemical outcome of the products has been explained by a suitable mechanism and supported by computational studies.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117115 |
| Deposited On: | 15 Apr 2021 07:59 |
| Last Modified: | 15 Apr 2021 07:59 |
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