Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

Tomoya Miura, Junki Nakahashi, Wang Zhoi, Yota Shiratori, Scott Stewart, Masahiro Murakami

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.

Original languageEnglish
Pages (from-to)10903-10908
Number of pages6
JournalJournal of the Amercian Chemical Society
Volume139
Issue number31
DOIs
Publication statusPublished - 2017

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