Palladium-catalyzed rearrangement and substitution reactions of acyclic vinylogous carbonates and sulfonates: Development of a new leaving group for Pd-allyl chemistry

Authors
Evans, PA Brandt, TA Robinson, JE
Citation
Pa. Evans et al., Palladium-catalyzed rearrangement and substitution reactions of acyclic vinylogous carbonates and sulfonates: Development of a new leaving group for Pd-allyl chemistry, TETRAHEDR L, 40(16), 1999, pp. 3105-3108
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3105 - 3108
Database
ISI
SICI code
0040-4039(19990416)40:16<3105:PRASRO>2.0.ZU;2-X
Abstract
Palladium-catalysed rearrangement of the deuterium labeled vinylogous carbo nate 1 furnished the beta-formyl esters 3a/b in 68% yield, while the Z-viny logous sulfonate (Z-VINS) 2 under analogous reaction conditions led to reve rsible O-alkylation and isomerization to afford the E-VINS 4a/b in 61% yiel d. This observation prompted the development of the vinylogous sulfonate as an improved leaving group for a variety of palladium-catalyzed allylic sub stitution reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.