Diastereoselective synthesis of pyrrolidines via the Yb(OTf)3 catalyzed three-component reaction of aldehydes, amines, and 1,1-cyclopropanediesters

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8242-8244

  Carson, Cheryl A ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 CYCLOPROPANEDIESTER; ALDEHYDE; AMINE; ESTER DERIVATIVE; IMINE; PYRROLIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CYCLOADDITION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

ALDEHYDES; AMINES; CATALYSIS; CYCLOPROPANES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRROLIDINES;

EID: 25444478111     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0512251     Document Type: Article

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17. 2 conditions employed by Carriera, it is quite possible that they would be satisfactory. The moisture- and air-tolerant nature of the lanthanide triflates was a strong factor in their selection as the catalysts of choice.
18. Generally it was not possible to separate the diastereomers using flash chromatography. The products appeared as single spots when analyzed by thin layer chromatography.