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Short and efficient route toward α-substituted N-arylazetidines from acetanilides via Mitsunobu reaction

N-Arylazetidines are efficiently obtained in a three-step procedure, providing a wide diversity of derivatives on multigram scale with overall yields of 21–55%. Cheap or easily available acetanilides are used in an adapted aldolization with aldehydes, furnishing β-hydroxyamides with an 81% average y...

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Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5519-5531
Main Authors: Kern, Nicolas, Hoffmann, Marie, Weibel, Jean-Marc, Pale, Patrick, Blanc, Aurélien
Format: Article
Language:English
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Summary:N-Arylazetidines are efficiently obtained in a three-step procedure, providing a wide diversity of derivatives on multigram scale with overall yields of 21–55%. Cheap or easily available acetanilides are used in an adapted aldolization with aldehydes, furnishing β-hydroxyamides with an 81% average yield over 21 examples. Special Mitsunobu conditions have been developed to ensure the cyclization of these hydroxyamides, giving β-lactams with an 73% average yield over 16 examples. A reduction then provided the N-arylazetidines in high yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.106