The highly enantioselective 1,3-dipolar cycloaddition of alkyl glyoxylate-derived nitrones to E-crotonaldehyde catalyzed by hybrid diamines

Tetrahedron Letters

Volumn 52, Issue 3, 2011, Pages 381-384

  Weseliński, Łukasz ^a   Słyk, Edyta ^a,b   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

1,3 Dipolar cycloaddition; Amino acids; Asymmetric organocatalysis; Binaphthyl derivatives; Nitrones

Indexed keywords

ALKYL GLYOXYLIC ACID; AMINO ACID DERIVATIVE; CROTONALDEHYDE; DIAMINE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; LEVO ALPHA AMINO ACID; NITRONE DERIVATIVE; PHENYLALANINE; UNCLASSIFIED DRUG;

1,3 DIPOLAR CYCLOADDITION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYBRID; STEREOCHEMISTRY;

EID: 78650231701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.015     Document Type: Article

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35. +: 267.1321, found: 267.1313. Optical purity (86% ee) was determined by HPLC analysis of its dibenzylic derivative.
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37. 4 in MeOH at 0 °C for 30 min. After aqueous work-up, the diastereomerically pure 3,4-trans-alcohol was purified by flash chromatography on silica gel (hexane-EtOAc) and isolated in 60-70% yield. The ee values of the alcohols were determined by chiral HPLC. All new compounds obtained here had correct analytical and spectral data. © 2010 Elsevier Ltd. All rights reserved.