Amine-catalyzed Michael reactions of an aminoaldehyde derivative to nitroolefins

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 693-696

  Albertshofer, Klaus ^a   Thayumanavan, Rajeswari ^a   Utsumi, Naoto ^a   Tanaka, Fujie ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amine; Aminoaldehyde; Asymmetric reactions; Enamine; Michael reaction; Nitroolefin

Indexed keywords

3 NITROTYROSINE; ALKENE; AMINE; AMINOALDEHYDE; ENAMINE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; THIOUREA;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33845648990     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.096     Document Type: Article

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35. 3): syn-isomer, δ 4.75 (ddd, J = 4.8 Hz, 9.3 Hz, 9.9 Hz, 1H), 4.94 (dd, J = 9.9 Hz, 13.2 Hz, 1H), 4.95 (d, J = 9.3 Hz, 1H), 5.24 (dd, J = 4.8 Hz, 1H), 7.08-7.18 (m, 5H), 7.67-7,76 (m, 4H), 9.72 (s, 1H); anti-isomer, δ 4.63-4.70 (m, 1H), 4.73-4.78 (m, 2H), 5.05 (d, J = 9.6 Hz, 1H), 7.35-7.42 (m, 5H), 7.79-7.92 (m, 4H), 9.47 (s, 1H). HPLC of the oxime of 2 with O-benzylhydroxylamine: Daicel Chiralpak AD, hexane/2-PrOH = 10:90, 1.0 mL/min, retention times: syn-2 major enantiomer 69.8 min; syn-2 minor enantiomer 25.9 min; anti-2 major enantiomer 57.9 min; anti-2 minor enantiomer 29.4 min.
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