1. Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from β-phosphonoamides.
- Author
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Avalos-Alanís, Francisco G., Hernández-Fernández, Eugenio, Hernández-Romero, Rocio, López-Cortina, Susana, Ordóñez, Mario, García-Barradas, Oscar, and Lagunas-Rivera, Selene
- Subjects
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OXAZOLINE synthesis , *AMIDES , *CHIRALITY , *CHEMICAL reactions , *DEHYDRATION reactions , *ALDEHYDES - Abstract
Abstract: Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-1a–h in good to excellent yields. The target compounds were prepared in good yield through the Horner–Wadsworth–Emmons reaction of β-phosphonoamide 3 bearing l-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-2a–h. Additionally, the cyclodehydration of β-phosphonoamide (S)-3 followed by the Horner–Wadsworth–Emmons reaction of β-phosphono-oxazoline (S)-4 with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-1a–h. [Copyright &y& Elsevier]
- Published
- 2014
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