Issue 96, 2018
From the journal:

Chemical Communications

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

Song Liu,a   Tao Zhang,a   Lei Zhu,a   Kangbao Zhong,a   Jianxian Gong, ORCID logo bc   Zhen Yang, ORCID logo *bc   Ruopeng Bai ORCID logo *a  and  Yu Lan ORCID logo *ad  

* Corresponding authors

a School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China
E-mail: ruopeng@cqu.edu.cn, lanyu@cqu.edu.cn

b Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
E-mail: zyang@pku.edu.cn

c 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

d 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.

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

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Article information

DOI
https://doi.org/10.1039/C8CC08335E
Article type
Communication
Submitted
18 Oct 2018
Accepted
09 Nov 2018
First published
12 Nov 2018

Chem. Commun., 2018,54, 13551-13554

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

S. Liu, T. Zhang, L. Zhu, K. Zhong, J. Gong, Z. Yang, R. Bai and Y. Lan, Chem. Commun., 2018, 54, 13551 DOI: 10.1039/C8CC08335E

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