Preparation of (3S,4S)-1-benzhydryl-3-[(5R)-1 '-hydroxyethyl]-4-acyl-2-azetidinones from (2R,3R)-epoxybutyramide precursors
(2000) Tetrahedron — Vol. 56, n° 20, p. 3209-3217 (2000)
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- The N-(phenacyl)-8a and N-(pivaloylmethyl)-8b derivatives of N-(benzhydryl)-(2R,3R)-cis-2,3-epoxybutyramide were prepared from sodium (2R,3R)-cis-2,3-epoxybutanoate 4. Under basic conditions they gave S(N)i reactions leading to the formation of four-, six- and seven-membered heterocycles, namely the azetidin-2-ones 9a, b (C-alkylation), the 2,3-dehydro-morpholin-5-ones 10a, b (O-alkylation), and the 4,5,6,7-tetrahydro-4-aza-oxepin-5-ones 12a, b (O-alkylation). The structures were confirmed by NMR analysis. Other rearrangement products, 13a and 14b, were also isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.
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Deng, B., Demillequand, M., Laurent, M., Touillaux, R., Belmans, M., Kemps, L., Cérésiat, M., & Marchand-Brynaert, J. (2000). Preparation of (3S,4S)-1-benzhydryl-3-[(5R)-1 ’-hydroxyethyl]-4-acyl-2-azetidinones from (2R,3R)-epoxybutyramide precursors. Tetrahedron, 56(20), 3209-3217. https://doi.org/10.1016/S0040-4020(00)00196-4 (Original work published 2000)