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Issue 2, 2014
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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

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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


Submitted
02 Oct 2013
Accepted
29 Oct 2013
First published
30 Oct 2013

Chem. Sci., 2014,5, 837-840
Article type
Edge Article

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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