Phenol-Directed Enantioselective Allylation of Aldimines and Ketimines

Phenols are effective directing and activating groups for our allylchlorosilane reagents, allowing the highly enantioselective allylation of a range of 2-aminophenol-derived aldimines. When the phenol is incorporated into the substrate ketimines may be allylated highly enantioselectively, leading to...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 26; pp. 6119 - 6121
Main Authors Rabbat, Philippe M. A, Valdez, S. Corey, Leighton, James L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.12.2006
Amer Chemical Soc
Subjects
Alkylation
Chemistry
Chemistry, Organic
Imines - chemistry
Phenols - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
BRONSTED ACID
ALDOL
TERT-BUTANESULFINYL IMINES
ASYMMETRIC-SYNTHESIS
OLEFIN METATHESIS CATALYSTS
CHIRAL ZIRCONIUM CATALYST
BETA-AMINO
AZA-DIELS-ALDER
MANNICH-TYPE
AMINO-ACID-DERIVATIVES
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Summary:Phenols are effective directing and activating groups for our allylchlorosilane reagents, allowing the highly enantioselective allylation of a range of 2-aminophenol-derived aldimines. When the phenol is incorporated into the substrate ketimines may be allylated highly enantioselectively, leading to the experimentally simple synthesis of a range of tertiary carbinamine structures.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol062589y