Sastry, G. Narahari ; Radha Krishna, Palakodety ; Reddy, P. Srinivas ; Narsingam, M. ; Sateesh, B. (2006) Diastereoselective Baylis-Hillman reaction: first use of sugar-derived α,β-unsaturated δ-lactone as chiral Michael acceptor Synlett, 17 (4). 0595-0599. ISSN 0936-5214
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Official URL: https://www.thieme-connect.com/products/ejournals/...
Related URL: http://dx.doi.org/10.1055/s-2006-933099
Abstract
Diastereoselective Baylis-Hillman reaction of sugar-derived α,β-unsaturated δ-lactone with several aromatic aldehydes in presence of DABCO (50 mol%) to afford adducts in moderate to good yields (49-75%) with 30-82% de is being reported for the first time. Quantum chemical calculations based on the stabilities of transition structures and on the stabilities of zwitterionic intermediates rationalized the experimental observations.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
| Keywords: | Sugar-Derived α,β-Unsaturated δ-Lactones; DiastereoSelective Baylis-Hillman Reactions; 2-C-Branched Glycosides; Zwitterion Intermediates; Computational Studies; Transition State Structures |
| ID Code: | 107144 |
| Deposited On: | 28 Jul 2017 06:15 |
| Last Modified: | 28 Jul 2017 06:15 |
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