Asymmetric γ-Deprotonation and Homoaldol Reaction of 1,3-Dien-2-yl Carbamates:  Stereo- and Regiochemistry

Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(−)-sparteine with a high degree of enantiotopic differentiation at the γ-position. They react with electrophiles regioselectively giving highly enantioenriched...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 8; no. 14; pp. 3061 - 3064
Main Authors Chedid, Roland Bou, Fröhlich, Roland, Hoppe, Dieter
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
Online AccessGet full text

Cover

More Information
Summary:Lithium compounds 7 are configurationally stable intermediates obtained by deprotonation of 1,3-dien-2-yl carbamates 6 with n-butyllithium/(−)-sparteine with a high degree of enantiotopic differentiation at the γ-position. They react with electrophiles regioselectively giving highly enantioenriched products. Starting with different isomers or changing the double-bond geometries in 6 leads to either of the enantiomers.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061005p