1′-Azido- and 1′-amino-1,3-dioxolan-4-ones

详细信息    查看全文

• 作者：Battaglia ; Arturo ; Barbaro ; Gaetano ; Giorgianni ; Patrizia ; Guerrini ; Andrea ; Pepe ; Antonella
• 刊名：Tetrahedron: Asymmetry
• 出版年：2001
• 出版时间：May 8, 2001
• 年：2001
• 卷：12
• 期：7
• 页码：1015-1023
• 全文大小：150 K

文摘

1,3-Dioxolanone alcohols, prepared via the addition of chiral lithium enolates of 1,3-dioxolan-4-ones to aldehydes, are suitable intermediates for the synthesis of chiral trisubstituted isoserines or trisubstituted 3-hydroxy-β-lactams. In particular, the methyl ester of 2-methyl-3-(2-furyl)isoserinic acid and two 3-methyl-3-hydroxy-β-lactams bearing either a 2-furyl or a phenyl substituent at C-(4) have been prepared. The (2R,3S) stereochemistry of the isoserine, and the (3R,4S) stereochemistry of the two β-lactams is that required for the synthesis of taxoid analogues having the side-chain with the proper (2′R,3′S) configuration.