Enantioselective construction of remote quaternary stereocentres

Tian-Sheng Mei, Harshkumar H. Patel and Matthew S. Sigman ()
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Tian-Sheng Mei: The University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112, USA
Harshkumar H. Patel: The University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112, USA
Matthew S. Sigman: The University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112, USA

Nature, 2014, vol. 508, issue 7496, 340-344

Abstract: Abstract Small molecules that contain all-carbon quaternary stereocentres—carbon atoms bonded to four distinct carbon substituents—are found in many secondary metabolites and some pharmaceutical agents. The construction of such compounds in an enantioselective fashion remains a long-standing challenge to synthetic organic chemists. In particular, methods for synthesizing quaternary stereocentres that are remote from other functional groups are underdeveloped. Here we report a catalytic and enantioselective intermolecular Heck-type reaction of trisubstituted-alkenyl alcohols with aryl boronic acids. This method provides direct access to quaternary all-carbon-substituted β-, γ-, δ-, ε- or ζ-aryl carbonyl compounds, because the unsaturation of the alkene is relayed to the alcohol, resulting in the formation of a carbonyl group. The scope of the process also includes incorporation of pre-existing stereocentres along the alkyl chain, which links the alkene and the alcohol, in which the stereocentre is preserved. The method described allows access to diverse molecular building blocks containing an enantiomerically enriched quaternary centre.

Date: 2014
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DOI: 10.1038/nature13231

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