Kyne, S. H., Miles, J. A. L., Percy, J. M. and Singh, K. (2012) Executing and rationalizing the synthesis of a difluorinated analogue of a ring-expanded calystegine B2. Journal of Organic Chemistry, 77 (2). pp. 991-998. ISSN 0022-3263
Full content URL: http://pubs.acs.org/doi/ipdf/10.1021/jo2022845
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J. Org. Chem. 2011 Kyne.pdf - Whole Document Restricted to Repository staff only 1MB |
Item Type: | Article |
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Item Status: | Live Archive |
Abstract
A difluorinated analogue of a ring-expanded calystegine B2 and some N-protected species were prepared via microwave-mediated transannular ring-opening of an epoxyketone. The diastereofacial selectivity of the epoxidation reaction, which delivers the key intermediate, and the regioselectivity of the transannular reactions were analyzed by density functional theory (DFT) methods. The epoxidation stereoselectivity arises from simple steric control, whereas the ring-closure reactions are subject to thermodynamic control.
Keywords: | Transannular ring-opening, Density functional theory, Epoxidation reaction |
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Subjects: | F Physical Sciences > F160 Organic Chemistry F Physical Sciences > F163 Bio-organic Chemistry |
Divisions: | College of Science > School of Chemistry |
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ID Code: | 17613 |
Deposited On: | 10 Jun 2015 14:50 |
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