Ghorai, Manas K. ; Halder, Sandipan ; Das, Raj Kumar (2010) Domino Imino-Aldol−Aza-Michael Reaction: One-Pot Diastereo- and Enantioselective Synthesis of Piperidines The Journal of Organic Chemistry, 75 (21). pp. 7061-7072. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo101680f
Related URL: http://dx.doi.org/10.1021/jo101680f
Abstract
Addition of α-arylmethylidene- or α-alkylidene-β-keto ester enolate to N-activated aldimines via the imino aldol pathway followed by intramolecular aza-Michael reaction in a domino fashion has been developed, and a highly diastereoselective route to substituted piperidines is reported. Enantiopure piperidines are synthesized from chiral sulfinyl imines. Formation and the observed stereoselectivity of the products have been rationalized by mechanistic and computational studies.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117120 |
| Deposited On: | 15 Apr 2021 08:01 |
| Last Modified: | 15 Apr 2021 08:01 |
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