Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid

Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid
Lilu Zhang, Xiao Zhang, Eric Meggers, Klaus Harms, Shipeng Luo, Yu Zheng
The enantioselective catalytic alkynylation of aromatic aldehydes is reported using a sterically highly hindered bis-cyclometalated rhodium-based Lewis acid catalyst featuring the octahedral metal as the only stereogenic center. Yields of 58–98% with 79–98% enantiomeric excess were achieved using 1–2 mol % of catalyst. This work complements previous work from our laboratory on the enantioselective alkynylation of 2-trifluoroacetyl imidazoles (Chem. - Eur. J. 2016, 22, 11977–11981) and trifluoromethyl ketones (J. Am. Chem. Soc. 2017, 139, 4322–4325) using catalysts with octahedral metal-centered chirality.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01394

DOI: 10.1021/acs.joc.7b01394

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