MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic gamma-butyrolactones

Authors
Maestro, MC Barquilla, MC Martin, MR
Citation
Mc. Maestro et al., MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic gamma-butyrolactones, TETRAHEDR-A, 10(18), 1999, pp. 3593-3599
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
18
Year of publication
1999
Pages
3593 - 3599
Database
ISI
SICI code
0957-4166(19990910)10:18<3593:MRO2WS>2.0.ZU;2-4
Abstract
Homochiral (SR)-4-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized car banions (from nitroalkanes, malononitrile and ethyl acetoacetate) afforded enantiopure bicyclic compounds in good yield (70-90%). 3-Oxabicyclic[3. 1.0 ]hexan-2-one derivatives were obtained with nitromethane and malonic acid d erivatives. However, dihydrofuro[3,4-d]isoxazol-6-one and dihydrofuro[3,4-b ]furan-6(4H)-one derivatives were obtained from nitroethane and ethyl aceto acetate, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.