Synthesis of enantiomerically pure alpha-amino-beta-hydroxycyclobutanone derivatives and their transformations into polyfunctional three- and five-membered ring compounds
(2004) Tetrahedron — Vol. 60, n° 35, p. 7591-7606 (2004)
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- Abstract
- Ketenes readily cycloadded to (R)-tert-butyldihydrooxazole 2a-d to yield enantiomerically pure bicyclic cyclobutanones. The cycloadditions proceeded with unusual regiochemistry giving predominantly or exclusively protected alpha-amino-beta-hydroxycyclobutanone derivatives. The adducts could be converted into a variety of interesting enantiopure intermediates equipped with many functional groups: alpha-amino-beta-hydroxy cyclopropane carboxylic acid derivatives, alpha-amino-beta-hydroxy succinic acid derivatives, alpha-amino-beta-hydroxy lactones and lactams derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
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Citations
Ghosez, L., Yang, G., Cagnon, J. R., Le Bideau, F., & Marchand-Brynaert, J. (2004). Synthesis of enantiomerically pure alpha-amino-beta-hydroxycyclobutanone derivatives and their transformations into polyfunctional three- and five-membered ring compounds. Tetrahedron, 60(35), 7591-7606. https://doi.org/10.1016/j.tet.2004.06.085 (Original work published 2004)