Ghorai, Manas K. ; Das, Kalpataru ; Kumar, Amit (2007) Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols Tetrahedron Letters, 48 (25). pp. 4373-4377. ISSN 0040-4039
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Official URL: http://doi.org/10.1016/j.tetlet.2007.04.097
Related URL: http://dx.doi.org/10.1016/j.tetlet.2007.04.097
Abstract
A highly efficient strategy for Cu(OTf)2 mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition reactions of enantiopure 2-phenyl-N-tosylazetidines with various aldehydes and ketones afforded a variety of substituted 1,3-oxazinanes and 1,3-amino alcohols in excellent yields, excellent de and good to excellent ee. The proposed SN2-type mechanism of the cycloaddition reaction is supported by experimental evidence.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier B.V. |
| Keywords: | N-tosylazetidine; Nucleophilic; Ring Opening; Carbonyl; Lewis Acid; Cu(Otf)2; [4+2] Cycloaddition; 1,3-oxazinane; 1,3-amino Alcohol; Non-racemic; Sn2; Mechanism. |
| ID Code: | 117129 |
| Deposited On: | 15 Apr 2021 08:02 |
| Last Modified: | 15 Apr 2021 08:02 |
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