Regioselective Baeyer-Villiger oxidation in 4-carbonyl-2-azetidinone series: a revisited route toward carbapenem precursor.
(2004) The Journal of Organic Chemistry — Vol. 69, n° 9, p. 3194-3197 (2004)
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- Abstract
- A novel synthesis of acetoxyazetidinone 2 is presented. The azetidinone ring of compounds 7 is formed by C-3/C-4 cyclization of (2R,3R)-epoxybutyramide precursors 6, N-protected with a benzhydryl group. N-Deprotection by photoactivated bromination and acidic treatment leads to compounds 10 with various CO-R substituents at C-4. Transformation of these substituents by Baeyer-Villiger oxidation gives the desired regioisomer 11 with the cyclopropyl side-group which is the only group (among R = H, Ph, t-Bu, i-Pr, c-Pr) able to satisfy both the steric requirements of the cyclization step and the electronic requirements of the oxidative rearrangement step.
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Laurent, M., Cérésiat, M., & Marchand-Brynaert, J. (2004). Regioselective Baeyer-Villiger oxidation in 4-carbonyl-2-azetidinone series: a revisited route toward carbapenem precursor. The Journal of Organic Chemistry, 69(9), 3194-3197. https://doi.org/10.1021/jo030377y (Original work published 2004)