Chemoselective allylic addition of allyltrichlorosilane to alpha-oxocarboxylic acids: synthesis of tertiary alpha-hydroxy carboxylic acids

Authors
Wang, Z Xu, GY Wang, DJ Pierce, ME Confalone, PN
Citation
Z. Wang et al., Chemoselective allylic addition of allyltrichlorosilane to alpha-oxocarboxylic acids: synthesis of tertiary alpha-hydroxy carboxylic acids, TETRAHEDR L, 41(23), 2000, pp. 4523-4526
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
23
Year of publication
2000
Pages
4523 - 4526
Database
ISI
SICI code
0040-4039(20000612)41:23<4523:CAAOAT>2.0.ZU;2-R
Abstract
Allyltrichlorosilane can add to alpha-oxocarboxylic acids in the presence o f DMF and HMPA. The alpha-carboxylic substituent exerts a remarkable neighb oring group effect on the reaction, The reaction presumably proceeds in an intramolecular fashion through a 'rigid' bicyclic transition state assembly involving a hypervalent silicate species, which produces the chemoselectiv ity approaching 100%. (C) 2000 Dupont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.