A novel synthetic route to chiral gamma-lactams from alpha-amino acids via Rh-catalyzed intramolecular C-H insertion.
A novel synthetic route to chiral gamma-lactams from alpha-amino acids via Rh-catalyzed intramolecular C-H insertion.
复制标题
通过 Rh 催化的分子内 C-H 插入从 α-氨基酸合成手性 γ-内酰胺的新路线。
DOI：
10.1021/jo0259717
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发表时间：
2002
期刊：
影响因子：
--
通讯作者：
Jung,KyungWoon
中科院分区：
文献类型：
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作者：
Yoon,CheolHwan;Flanigan,DavidL;Chong,Byong-Don;Jung,KyungWoon
高功能化γ-内酰胺是合成许多具有重要生物学意义的天然产物的关键中间体。本文描述了通过α-氨基酸衍生的具有不同官能团的α-重氮-α-（苯基磺酰基）乙酰酰胺的分子内C−H插入合成各种手性γ-内酰胺。环化反应具有高度的区域选择性和立体选择性，可获得高收率的手性γ-内酰胺基序。
Highly functionalized γ-lactams are key intermediates for the synthesis of numerous biologically significant natural products. We herein described the synthesis of various chiral γ-lactams via intramolecular C−H insertion of α-diazo-α-(phenylsulfonyl)acetamides derived from α-amino acids, which possess various functional groups. The cyclizations were highly regio- and stereoselective to afford chiral γ-lactam motifs in high yields.