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; Masahiro Murakami

doi:10.1021/ja405790t

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

J Am Chem Soc. 2013 Aug 7;135(31):11497-500. doi: 10.1021/ja405790t. Epub 2013 Jul 30.

Authors

Tomoya Miura¹, Yui Nishida, Masao Morimoto, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. tmiura@sbchem.kyoto-u.ac.jp

PMID: 23886015
DOI: 10.1021/ja405790t

Abstract

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.