Investigation of a dialkylation approach for enantioselective constructionof vicinal quaternary stereocenters

Authors
Hoyt, SB Overman, LE
Citation
Sb. Hoyt et Le. Overman, Investigation of a dialkylation approach for enantioselective constructionof vicinal quaternary stereocenters, ORG LETT, 2(20), 2000, pp. 3241-3244
Citations number
8
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3241 - 3244
Database
ISI
SICI code
1523-7060(20001005)2:20<3241:IOADAF>2.0.ZU;2-L
Abstract
[GRAPHICS] A detailed study of the dialkylation of dianions derived from dihydroisoind igo 1 with enantiopure ditriflate 2 is reported. The LHMDS-mediated process has been optimized to give C-2-symmetric product 3 with high selectivity ( C-2 selectivity 3:5 = 100:1; C-2:C-1 selectivity = 8:1). Stereoselection in the C-2 manifold is determined in both the bimolecular and intramolecular alkylation steps.