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Organocatalytic Regiodivergent C−C Bond Cleavage of Cyclopropenones: A Highly Efficient Cascade Approach to Enantiopure Heterocyclic Frameworks
Author(s) -
Cao Jian,
Fang Ran,
Liu JinYu,
Lu Hong,
Luo YongChun,
Xu PengFei
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803861
Subject(s) - enantiopure drug , regioselectivity , catalysis , chemistry , cycloaddition , bifunctional , ring (chemistry) , combinatorial chemistry , cascade , ring strain , cascade reaction , bond cleavage , hydrogen bond , stereochemistry , enantioselective synthesis , organic chemistry , molecule , chromatography
Here a highly efficient cascade approach is reported that combines a cycloaddition reaction with a regioselective strain‐release process to afford diverse heterocyclic frameworks through bifunctional catalysis. The cooperation of hydrogen‐bonding network activation and a regiodivergent strain‐assisted effect is the key to promoting this complex chemical transformation, leading to the generation of two different ring systems in high yields with excellent stereoselectivities. The reaction proceeded by a mechanism involving a “spring‐loaded” intermediate with switchable C−C bond cleavages achieved by controllable ring‐strain release. This reaction was also amenable to gram scale synthesis with only 0.1 mol % catalyst loading.