Ghorai, Manas K. ; Das, Kalpataru ; Shukla, Dipti (2007) Lewis Acid-Mediated Highly Regioselective SN2-Type Ring-Opening of 2-Aryl-N-tosylazetidines and Aziridines by Alcohols The Journal of Organic Chemistry, 72 (15). pp. 5859-5862. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo0703294
Related URL: http://dx.doi.org/10.1021/jo0703294
Abstract
Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar SN2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee. The mechanism of the ring-opening of aziridines and azetidines via an SN2 pathway is supported by the formation of nonracemic amino ethers.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117128 |
| Deposited On: | 15 Apr 2021 08:02 |
| Last Modified: | 15 Apr 2021 08:02 |
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