Sreenithya, A. ; Sunoj, Raghavan B. (2012) Noninnocent role of N-methyl pyrrolidinone in thiazolidinethione-promoted asymmetric aldol reactions Organic Letters, 14 (22). pp. 5752-5755. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol302761n
Related URL: http://dx.doi.org/10.1021/ol302761n
Abstract
The origin of stereoselectivity in the reaction between α-azido titanium enolate derived from chiral auxiliary N-acyl thiazolidinethione and benzaldehyde is established using the DFT (B3LYP) method. A nonchelated transition state with N-methyl-2-pyrrolidinone (NMP) bound to a TiCl3 enolate is found to be energetically the most preferred model responsible for the formation of an Evans syn aldol product. The TS model devoid of NMP, although of higher energy, is found to be successful in predicting the right stereochemical outcome.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 109761 |
| Deposited On: | 02 Aug 2017 11:50 |
| Last Modified: | 02 Aug 2017 11:50 |
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