Journal
TETRAHEDRON
Volume 69, Issue 45, Pages 9381-9390Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.08.084
Keywords
Nitrones; Isoxazolidines; Pyrrolidines
Categories
Funding
- Ministerio de Ciencia e Innovacion (MICINN)
- FEDER Program (Madrid, Spain) [CTQ2010-19606, BFU2010-19504]
- Gobierno de Aragon (Zaragoza, Spain. Bioorganic Chemistry Group) [E-10]
- MIUR (Italy)
- CNMPS (Italy)
- MICINN
- University of Palermo
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Diastereoselective asymmetric 1,3-dipolar cycloadditions of N-(alkoxycarbonylmethyl) nitrones derived from glycine, alanine and phenylalanine have been studied both experimentally and theoretically. Asymmetric induction is evaluated by either introducing a chiral group at the nitrone nitrogen atom or by using Oppolzer's sultam acrylamide. In both cases the sense of the asymmetric induction is the same, the (3R,5R)-isomer being preferentially obtained. The best results were observed with the chiral dipolarophile, which afforded an only isomer in all cases. The obtained isoxazolidines are easily transformed into the corresponding 5-substituted-3-hydroxypyrrolidin-2-ones. DFT studies are in a qualitative agreement with the observed experimental results. (C) 2013 Elsevier Ltd. All rights reserved.
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