Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

Authors
Cohen, F MacMillan, DWC Overman, LE Romero, A
Citation
F. Cohen et al., Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans, ORG LETT, 3(8), 2001, pp. 1225-1228
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
8
Year of publication
2001
Pages
1225 - 1228
Database
ISI
SICI code
1523-7060(20010419)3:8<1225:SITPSO>2.0.ZU;2-M
Abstract
Depending upon the nature of the alkene and allylic substituents, acid-prom oted rearrangements of acetals derived from anti allylic diols give 12 or s tereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the ally lic substituents and the extent of bonding in the Prins cyclization transit ion state are central features of a proposed new model for predicting stere oselection in the Prins-pinacol synthesis of acyltetrahydrofurans.