A new addition-carbocyclization cascade reaction initiated by arylboronic acids and catalyzed by a rhodium/chiral diene complex is described. Starting from N-bridged oxoenoate derivatives, highly functionalized piperidines bearing three contiguous stereogenic centers were obtained with excellent enantio- and diastereoselectivities.
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http://dx.doi.org/10.1021/acs.orglett.5b02858 | DOI Listing |
Org Lett
November 2015
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 11 rue Pierre et Marie Curie, 75005, Paris, France.
A new addition-carbocyclization cascade reaction initiated by arylboronic acids and catalyzed by a rhodium/chiral diene complex is described. Starting from N-bridged oxoenoate derivatives, highly functionalized piperidines bearing three contiguous stereogenic centers were obtained with excellent enantio- and diastereoselectivities.
View Article and Find Full Text PDFChemMedChem
November 2013
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS 10/1, Sector 10, Jankipuram Extension, Sitapur Rd, Lucknow 226031 (India).
A controlled cascade: A divergent, diastereoselective and efficient one-pot synthesis of allocolchicinoids via a cascade Suzuki-Michael addition-Carbocyclization sequence is described. The utility of the compounds as possible inhibitors of insulin aggregation is also presented.
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