Diastereoselectivity enhancement in the 1,3-cycloaddition of β-lactam aldehydes.: Application to the synthesis of enantiopure indolizidinone amino esters
Diastereoselectivity enhancement in the 1,3-cycloaddition of β-lactam aldehydes.: Application to the synthesis of enantiopure indolizidinone amino esters
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DOI：
10.1021/jo051402y
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发表时间：
2005-10-28
影响因子：
3.6
通讯作者：
Ruiz, MP
中科院分区：
文献类型：
--
作者：
Alcaide, B;Almendros, P;Ruiz, MP
通过噻唑基单碳同源反应制备了对映纯α -烷氧基- β -内酰胺乙醛。由α -烷氧基β -内酰胺乙醛衍生的偶氮亚胺酰基酯进行1,3-偶极环加成反应，得到了具有良好非对映选择性的高度功能化的2-氮化丁酮系脯氨酸，这些脯氨酸被直接用于首次从β -内酰胺中制备氮杂环[4.3.0]-壬烷（吲哚吡啶酮）氨基酯。
Enantiopure alpha-alkoxy,beta-lactam acetaldehydes were prepared via the thiazole-based one-carbon homologation. The 1,3-dipolar cycloaddition reaction involving (alpha-alkoxy beta-lactam acetaldehyde-derived azomethine ylides gave with excellent diastereoselectivity highly functionalized 2-azetidinone-tethered prolines, which were directly used for the first preparation of azabicyclo[4.3.0]-nonane (indolizidinone) amino esters from beta-lactams.