Hetero Dielsȁ3;Alder reactions of acyl phosphonates: synthesis of glycosyl type phosphonates

详细信息    查看全文

• 作者：Sidika Polat-Cakir^a ; ^b ; Ayhan S. Demir^b ; ^{asdemir@metu.edu.tr}
• 关键词：Acyl phosphonates ; Hetero Dielsȁ3 ; Alder ; Glycosyl phosphonates
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：1 April 2011
• 年：2011
• 卷：67
• 期：13
• 页码：2396-2401
• 全文大小：661 K

文摘

We have prepared glycosyl type phosphonates via hetero Dielsȁ3;Alder (HDA) reactions of acyl phosphonates with electron rich dienes. HDA reactions of acyl phosphonates with Danishefsky’s diene required thermal activation to yield the desired dihydropyranones in good yield (70ȁ3;91 % ). The reactions with Brassard’s diene involved Lewis acid promotion to yield the corresponding lactones, though in moderate yield (33ȁ3;69 % ).