Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols

Authors
Hogberg, HE Lindmark, M Isaksson, D Sjodin, K Franssen, MCR Jongejan, H Wijnberg, JBPA de Groot, A
Citation
He. Hogberg et al., Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols, TETRAHEDR L, 41(17), 2000, pp. 3193-3196
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
17
Year of publication
2000
Pages
3193 - 3196
Database
ISI
SICI code
0040-4039(20000422)41:17<3193:FOHEIL>2.0.ZU;2-1
Abstract
Normally many lipases are efficient catalysts for the acetylation of alcoho ls with vinyl acetate. Unexpectedly, we found that some sterically hindered secondary alcohols react slowly to yield hemiacetal esters as mixtures of diastereomers. Their formation can be explained by the reaction of the alco hol with acetaldehyde that is produced by the lipase-catalysed splitting of vinyl acetate and subsequent acetylation of the resulting hemiacetal by th e lipase. (C) 2000 Elsevier Science Ltd. All rights reserved.