Reaction of Baylis-Hillman products with Swern and Dess-Martin oxidants

Authors
Lawrence, NJ Crump, JP McGown, AT Hadfield, JA
Citation
Nj. Lawrence et al., Reaction of Baylis-Hillman products with Swern and Dess-Martin oxidants, TETRAHEDR L, 42(23), 2001, pp. 3939-3941
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
23
Year of publication
2001
Pages
3939 - 3941
Database
ISI
SICI code
0040-4039(20010604)42:23<3939:ROBPWS>2.0.ZU;2-2
Abstract
The Baylis-Hillman adducts of aryl aldehydes and alkyl acrylates are effici ently oxidized to the corresponding alpha -methylene-beta -keto esters with the Dess-Martin periodinane. The attempted Swern oxidation of the same add ucts resulted in S(N)2 ' -type substitution of the allylic hydroxyl group b y chloride. (C) 2001 Elsevier Science Ltd. All rights reserved.