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Chem Commun (Camb). 2018 Dec 14;54(96):13551-13554. doi: 10.1039/c8cc08335e. Epub 2018 Nov 16.

Retro-metal-ene versus retro-Aldol: mechanistic insight into Rh-catalysed formal [3+2] cycloaddition.

Author information

1
School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China. ruopeng@cqu.edu.cn lanyu@cqu.edu.cn.
2
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China. zyang@pku.edu.cn and State Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and the Peking University, Beijing 100871, China.
3
School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China. ruopeng@cqu.edu.cn lanyu@cqu.edu.cn and College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China.

Abstract

Theoretical calculations have been performed to investigate the mechanism and stereoselectivity of rhodium-catalysed intramolecular [3+2] cycloaddition for construction of a substituted hexahydropentalene complex. A new C-C bond cleavage mechanism, retro-Aldol-type, is proposed and verified for this Rh-catalysed [3+2] cycloaddition reaction.

PMID:
30444245
DOI:
10.1039/c8cc08335e

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