Issue 2, 2014
From the journal:

Chemical Science

Exploitation of Rh(i)–Rh(iii) cycles in enantioselective C–C bond cleavages: access to β-tetralones and benzobicyclo[2.2.2]octanones†

Laetitia Souillarta  and  Nicolai Cramer*a  

* Corresponding authors

a Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSA, BCH 4305, CH-1015 Lausanne, Switzerland
E-mail: nicolai.cramer@epfl.ch

Abstract

Rhodium(I)-catalyzed β-carbon eliminations of tert-cyclobutanols followed by oxidative addition give benzorhoda(III)cyclopentenes. These key intermediates trigger intramolecular C–H arylations leading to β-tetralones with quaternary stereogenic centers in excellent enantioselectivity. The versatility of the rhoda(III)cyclic species is further shown in formal intramolecular [4+2]-cycloadditions providing access to benzobicyclo[2.2.2]octanones.

Graphical abstract: Exploitation of Rh(i)–Rh(iii) cycles in enantioselective C–C bond cleavages: access to β-tetralones and benzobicyclo[2.2.2]octanones

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Article information

DOI
https://doi.org/10.1039/C3SC52753K
Article type
Edge Article
Submitted
02 Oct 2013
Accepted
29 Oct 2013
First published
30 Oct 2013

Chem. Sci., 2014,5, 837-840

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Exploitation of Rh(I)–Rh(III) cycles in enantioselective C–C bond cleavages: access to β-tetralones and benzobicyclo[2.2.2]octanones

L. Souillart and N. Cramer, Chem. Sci., 2014, 5, 837 DOI: 10.1039/C3SC52753K

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