A combination of homogeneous hydrogenation and metathesis reactions allows highly efficient, stepwise chemo- and stereoselective formation of three separate 2,7-diaminosuberic acid derivatives in a single pot without isolation of intermediates.
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http://dx.doi.org/10.1039/b510420c | DOI Listing |
J Am Chem Soc
August 2013
Department of Chemistry, 6-331, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
n-Alkyl arenes were prepared in a one-pot tandem dehydrogenation/olefin metathesis/hydrogenation sequence directly from alkanes and ethylbenzene. Excellent selectivity was observed when ((tBu)PCP)IrH2 was paired with tungsten monoaryloxide pyrrolide complexes such as W(NAr)(C3H6)(pyr)(OHIPT) (1a) [Ar = 2,6-i-Pr2C6H3; pyr = pyrrolide; OHIPT = 2,6-(2,4,6-i-Pr3C6H2)2C6H3O]. Complex 1a was also especially active in n-octane self-metathesis, providing the highest product concentrations reported to date.
View Article and Find Full Text PDFChem Commun (Camb)
May 2006
TU Berlin - Berlin University of Technology, Institute of Chemistry, Strasse des 17. Juni 115, Sekr. C3, 10623 Berlin, Germany.
A total synthesis of (-)-centrolobine (1) based on a diastereoselective ring rearrangement metathesis-double bond isomerisation sequence and a one-pot cross metathesis-hydrogenation procedure is described.
View Article and Find Full Text PDFChem Commun (Camb)
November 2005
School of Chemistry, Monash University, Clayton 3800, Victoria, Australia.
A combination of homogeneous hydrogenation and metathesis reactions allows highly efficient, stepwise chemo- and stereoselective formation of three separate 2,7-diaminosuberic acid derivatives in a single pot without isolation of intermediates.
View Article and Find Full Text PDFOrg Lett
February 2003
Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
[reaction: see text] A one-pot tandem cross-metathesis/hydrogenation/cyclization procedure was achieved at room temperature, under 1 atm of hydrogen, in the presence of a ruthenium catalyst and PtO(2) showing the compatibility of the two catalysts. This tandem reaction allows the synthesis of substituted lactones and lactols from acrylic acid and acrolein, respectively, in the presence of unsaturated alcohols.
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