Practical and efficient synthesis of chiral 2,4-disubstituted oxazolines from 尾-phosphonoamides

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• 作者：Francisco G. Avalos-Alan铆s ; Eugenio Hern谩ndez-Fern谩ndez ; Rocio Hern谩ndez-Romero ; Susana L贸pez-Cortina ; Mario Ord贸帽ez ; Oscar Garc铆a-Barradas ; Selene Lagunas-Rivera
• 刊名：Tetrahedron: Asymmetry
• 出版年：31 January, 2014
• 年：2014
• 卷：25
• 期：2
• 页码：156-162
• 全文大小：749 K

文摘

Herein we report a practical and efficient method for the synthesis of optically active 2,4-disubstituted oxazolines (S)-ng class="boldFont">1ang>-ng class="boldFont">hng> in good to excellent yields. The target compounds were prepared in good yield through the Horner-Wadsworth-Emmons reaction of 尾-phosphonoamide ng class="boldFont">3ng> bearing l-phenylalaninol with commercially available aryl aldehydes followed by the cyclodehydration of the corresponding N-(cinnamoyl)-(S)-phenylalaninol derivatives (S)-ng class="boldFont">2ang>-ng class="boldFont">hng>. Additionally, the cyclodehydration of 尾-phosphonoamide (S)-ng class="boldFont">3ng> followed by the Horner-Wadsworth-Emmons reaction of 尾-phosphono-oxazoline (S)-ng class="boldFont">4ng> with aryl aldehydes also gave the 2,4-disubstituted oxazolines (S)-ng class="boldFont">1ang>-ng class="boldFont">hng>.