Synthesis of cyclopentane annulated δ-lactams via diazomethane-mediated C-C bond cleavage of α-keto N,O-hemiaminals

被引：0
|
作者：
Gorle, Hari Mangeswara Rao [1 ,2 ]
Marok, Satwinder Singh [3 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur, India
[2] Texila Amer Univ, Dept Chem, Georgetown, Guyana
[3] Apotex Inc, Toronto, ON, Canada
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2024年 / 61卷 / 07期
关键词：
CATALYTIC ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; AMIDOALKYLATION REAGENTS; N-BOC; ACID; ALCOHOLS; IMINES;
D O I：
10.1002/jhet.4829
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diazomethane-mediated C-C bond cleavage of alpha-keto N,O-hemiaminals was investigated for the first time. Diazomethane as a reagent result C-C bond cleavage of norbornyl alpha-keto N,O-hemiaminals, Grob-like fragmentation, lead to the formation of cyclopentane annulated delta-lactams in excellent yields. We have synthesized the precursor norbornyl alpha-keto N,O-hemiaminal by the nucleophilic displacement of halogen of norbornyl alpha-diketone with the various amines.
引用
收藏
页码：1070 / 1074
页数：5
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