Abnormal Claisen rearrangements of tetronates and stereoselective ring opening of intermediate spirocyclopropanes

Authors
Schobert, R Siegfried, S Gordon, G Mulholland, D Nieuwenhuyzen, M
Citation
R. Schobert et al., Abnormal Claisen rearrangements of tetronates and stereoselective ring opening of intermediate spirocyclopropanes, TETRAHEDR L, 42(27), 2001, pp. 4561-4564
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
27
Year of publication
2001
Pages
4561 - 4564
Database
ISI
SICI code
0040-4039(20010702)42:27<4561:ACROTA>2.0.ZU;2-G
Abstract
Thermal [2,3]-sigmatropic rearrangements of allyltetronates proceed via 3-( spirocyclopropyl)dihydrofuran-2,4-diones; in some cases these could be isol ated and their cyclopropane rings stereoselectively opened with alcohols or water to give 3-(beta -syn-alkoxy)tetronic acids. Treatment of a 5,5-disub stituted benzyltetronate with LDA also produced a 3-substituted tetronic ac id by an anionic [1,3]-rearrangement. (C) 2001 Elsevier Science Ltd. All ri ghts reserved.