The alkylation of a novel acetal derived from (2R,3R)-(+)-tartaric acid: An unexpected rearrangement

Authors
Barros, MT Burke, AJ Maycock, CD
Citation
Mt. Barros et al., The alkylation of a novel acetal derived from (2R,3R)-(+)-tartaric acid: An unexpected rearrangement, TETRAHEDR L, 40(8), 1999, pp. 1583-1586
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
8
Year of publication
1999
Pages
1583 - 1586
Database
ISI
SICI code
0040-4039(19990219)40:8<1583:TAOANA>2.0.ZU;2-M
Abstract
The novel chiral bis-acetal dioxane 2a derived from (2R,3R)-(+)-tartaric ac id was shown to undergo an unexpected rearrangement upon treatment with lit hium amide base to give the chiral dioxolane 3a in optically active form. A lkylation and aldol studies were performed on the diisopropyl ester of this dioxolane 3b. (C) 1999 Elsevier Science Ltd. All rights reserved.