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Enantioselective Synthesis of Anti Homoallylic Alcohols from Terminal Alkynes and Aldehydes Based on Concomitant Use of a Cationic Iridium Complex and a Chiral Phosphoric Acid

Tomoya Miura*, Yui Nishida, Masao Morimoto and Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: tmiurasbchem.kyoto-u.ac.jp, murakamisbchem.kyoto-u.ac.jp

T. Miura, Y. Nishida, M. Morimoto, M. Murakami, J. Am. Chem. Soc., 2013, 135, 11497-11500.

DOI: 10.1021/ja405790t (free Supporting Information)



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Abstract

A cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates followed by a chiral phosphoric acid-catalyzed allylation reaction of aldehydes enables a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols.

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Key Words

homoallylic alcohols


ID: J48-Y2013