One pot synthesis of optically active 4-isoxazolines by asymmetric addition of alkynylzinc reagents to nitrones followed by cyclization

Heterocycles

Volumn 78, Issue 3, 2009, Pages 717-724

  Wei, Weilin ^a   Kobayashi, Masato ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Alkynylzinc Reagent; Asymmetric Addition to Nitrone; Cyclization; One Pot Synthesis; Optically Active 4 Isoxazoline

Indexed keywords

EID: 65549114098     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-11566     Document Type: Article

References (15)

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13. The absolute stereochemistry of the obtained 4-isoxazolines 5 was determined to be S, because the inversion of the stereochemistry was in principle impossible during the cyclization.
14. Partial racemization might have slightly occurred during this step.
15. The precise mechanism of the asymmetric addition reaction to nitrones 2 is still an open question. Especially, the role of the methylzinc salt of a product-like racemic hydroxylamine 4 in the enantiomeric enhancement remains to be accounted for. The easier assembly of the methylzinc salts of a racemic mixture of the product-like hydroxylamines compared with that of the optically pure (R)- or (S) hydroxylamine seems to be noteworthy for such the phenomenon.