Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation

Jung Tae Han, Won Jun Jang, Namhyeon Kim, Jaesook Yun

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Abstract

An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.

Original languageEnglish
Pages (from-to)15146-15149
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number46
DOIs
StatePublished - 23 Nov 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

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