Premium
Formal [3+2] Cycloaddition Between in situ Formed 1,4‐Benzodiazepin‐2‐One‐Based Azomethine Ylides and Azodicarboxylic Acid Derivatives: Diastereoselective Synthesis of Spiro‐1,4‐Benzodiazepin‐2‐Ones
Author(s) -
Fan XiaoZu,
Wu HuiHui,
Tang Zhe,
Zhang Heng,
Cai LuYu,
Bi XiaoFan,
Zhao HongWu
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001486
Subject(s) - chemistry , cycloaddition , yield (engineering) , in situ , stereochemistry , crystal structure , reaction conditions , molecule , reaction mechanism , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
In the presence of PhCO 2 H (20 mol%), the formal [3+2] cycloaddition between in situ formed 1,4‐benzodiazepin‐2‐one‐based azomethine ylides and azodicarboxylic acid derivatives proceeded readily, thus leading to the formation of trans ‐configured spiro‐1,4‐benzodiazepin‐2‐ones in up to 98% chemical yield with >20:1 dr . The relative configuration of the title compounds was unambiguously determined by means of X‐ray single crystal structure analysis. The reaction mechanism was hypothesized to account for the diastereoselective formation of the isolated spiro‐1,4‐benzodiazepin‐2‐ones.