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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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Published in: | Tetrahedron 2014-09, Vol.70 (35), p.5519-5531 |
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Main Authors: | , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2014.06.106 |