Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones

Authors
Alibes, R de March, P Figueredo, M Font, J Racamonde, M
Citation
R. Alibes et al., Stereoselective [2+2] photocycloaddition of acetylene to chiral 2(5H)-furanones, TETRAHEDR L, 42(38), 2001, pp. 6695-6697
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
38
Year of publication
2001
Pages
6695 - 6697
Database
ISI
SICI code
0040-4039(20010917)42:38<6695:S[POAT>2.0.ZU;2-Q
Abstract
The photochemical [2+2] cycloaddition of acetylene to chiral 2(5H)-furanone s is investigated. The effect of the substituent at the stereogenic center of the lactone on the chemical yield and facial diastereo selectivity is ev aluated. Using a C-2-symmetric bis-lactone as substrate, a diastereomeric e xcess higher than 98% is found. (C) 2001 Elsevier Science Ltd. All rights r eserved.