Copper(I)-catalyzed enantioselective synthesis of α-chiral linear or carbocyclic (e)-(γ-alkoxyallyl)boronates

Eiji Yamamoto, Yuta Takenouchi, Taichi Ozaki, Takanori Miya, Hajime Ito

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56 Citations (Scopus)

Abstract

A new method has been developed for the catalytic asymmetric synthesis of α-chiral linear or carbocyclic (γ-alkoxyallyl)boronates via the copper(I)-catalyzed γ-boryl substitution of allyl acetals. This reaction afforded the products in high yields with excellent E:Z selectivities and enantioselectivities [only (E)-product, 91-98% ee] and also exhibited high functional group compatibility. Subsequent allylation of aldehydes with the α-chiral (γ-alkoxyallyl)boronates provided the anti-1,2-diol derivatives in a highly stereospecific manner, and the utility of the α-chiral (γ-alkoxyallyl)boronates was further demonstrated by a convergent coupling of a complex polyol derivative using a (γ-alkoxyallyl)boronate and a chiral α-oxyaldehyde. The stereoselective modular construction of a complex 3,3-disubstituted cyclopentene containing three consecutive stereocenters including a quaternary chiral carbon was also reported. Useful transformations of the α-chiral linear (γ-alkoxyallyl)boronates were also demonstrated.

Original languageEnglish
Pages (from-to)16515-16521
Number of pages7
JournalJournal of the American Chemical Society
Volume136
Issue number47
DOIs
Publication statusPublished - Nov 26 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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