Massive Parallel Catalyst Screening:  Toward Asymmetric MCRs

Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane was found to give enantiomeric excesses between 32% and 42%...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 22; pp. 4021 - 4024
Main Authors Kusebauch, Ulrike, Beck, Barbara, Messer, Kim, Herdtweck, Eberhardt, Dömling, Alexander
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.10.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MULTICOMPONENT REACTIONS
ACID
PASSERINI-REACTION
ISOCYANIDES
STEREOSELECTIVE SYNTHESES
CONDENSATIONS
UGI-REACTION
ADDITIONS
TITANIUM
Online AccessGet full text

Cover

More Information
Summary:Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane was found to give enantiomeric excesses between 32% and 42% in several examples. The absolute stereo induction of one example was determined chemically and by means of X-ray crystallography. This comprises the first asymmetric Passerini reaction and the first example of a stereochemical induction in an isocyanide based multicomponent reaction by a chiral Lewis acid.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035010u