Issue 2, 2016

Rh(iii)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

Abstract

The Rh(III)-catalyzed cascade addition of a C–H bond across alkene and carbonyl π-bonds is reported. The reaction proceeds under mild reaction conditions with low catalyst loading. A range of directing groups were shown to be effective as was the functionalization of alkenyl in addition to aromatic C(sp2)–H bonds. When the enone and aldehyde electrophile were tethered together, cyclic β-hydroxy ketones with three contiguous stereocenters were obtained with high diastereoselectivity. The intermolecular three-component cascade reaction was demonstrated for both aldehyde and imine electrophiles. Moreover, the first X-ray structure of a cationic Cp*Rh(III) enolate with interatomic distances consistent with an η3-bound enolate is reported.

Graphical abstract: Rh(iii)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

Supplementary files

Article information

Article type
Edge Article
Submitted
31 Okt. 2015
Accepted
23 Nov. 2015
First published
01 Dec. 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 1474-1479

Rh(III)-catalyzed diastereoselective C–H bond addition/cyclization cascade of enone tethered aldehydes

J. A. Boerth and J. A. Ellman, Chem. Sci., 2016, 7, 1474 DOI: 10.1039/C5SC04138D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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