Regio- and enantioselective copper-catalyzed addition of dialkylzinc reagents to cyclic 2-alkenyl aziridines

Tetrahedron Letters

Volumn 44, Issue 47, 2003, Pages 8559-8562

  Gini, Francesca ^a   Del Moro, Federica ^a   Macchia, Franco ^a   Pineschi, Mauro ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; AZIRIDINE DERIVATIVE; COPPER COMPLEX; PHOSPHORAMIDIC ACID DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; KINETICS; STEREOCHEMISTRY;

EID: 0142231047     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.133     Document Type: Article

References (31)

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20. 2. In this reaction also an unidentified product was obtained (ca. 20% of the crude mixture).
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27. 6) δ 163.6, 142.8, 137.3, 129.1, 128.9, 128.5, 127.9, 114.8, 68.4, 42.1, 39.2, 29.8 23.9, 20.9.
28. 3) δ 156.5; 137.3; 137.1; 129.2; 128. 8; 128.1; 67.3; 48.1; 30.7; 30.2; 21.9. The enantiomeric excess was determined by HPLC on a Daicel Chiralcel OD-H (hexanes/IPA=98:2). Retention times were: 31 min (major), 42 min (minor).
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31. 3). Major ( 7 ): δ 7.36-7.26 (m, 5H), 5.33-5.30 (m, 1H), 5.08 (s, 2H), 4.80-4.70 (m, 1H), 4.30-4.10 (m, 1H), 2.07-1. 13 (m, 10H), 0.87 (t, 3H, J=7.3 Hz). Minor ( 8 ): 3.65-3.85 (m, 1H), 4.81 (s, 1H), 5.15 (s, 1H).