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Copper‐Catalyzed Enantioselective [2+2] Cycloadditions of 2‐Nitrosopyridine with Ketenes
Author(s) -
Chatterjee Indranil,
Jana Chandan Kumar,
Steinmetz Marc,
Grimme Stefan,
Studer Armido
Publication year - 2010
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.201000153
Subject(s) - chemistry , enantioselective synthesis , catalysis , copper , density functional theory , computational chemistry , cycloaddition , combinatorial chemistry , organic chemistry
Copper(I)‐catalyzed [2+2] cycloadditions of various ketenes with 2‐nitrosopyridine to afford synthetically highly valuable 1,2‐oxazetidine‐3‐ones are shown to occur with good enantioselectivities. The thermal uncatalyzed process furnishes the unstable regioisomeric oxazetidinone. Density function theory (DFT) calculations give evidence that the reaction occurs via a concerted [2+2] cycloaddtion pathway.