Mechanistic insights into the factors determining exo-endo selectivity in the Lewis acid-catalyzed Diels-Alder reaction of 1,3-dienes with 2-cycloalkenones

Authors
Ge, M Stoltz, BM Corey, EJ
Citation
M. Ge et al., Mechanistic insights into the factors determining exo-endo selectivity in the Lewis acid-catalyzed Diels-Alder reaction of 1,3-dienes with 2-cycloalkenones, ORG LETT, 2(13), 2000, pp. 1927-1929
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
13
Year of publication
2000
Pages
1927 - 1929
Database
ISI
SICI code
1523-7060(20000629)2:13<1927:MIITFD>2.0.ZU;2-W
Abstract
We adduce evidence that the asynchronous, Lewis acid-catalyzed Diets-Alder reaction of 2-cycloalkenones with nonsimple alpha,beta-enones can proceed v ia transition states in which the 1,3-diene subunit is skewed, i.e., nonpla nar, with profound effects on the ratio of exo and endo addition products.