Stereoselective aldol-type cyclization reaction mediated by dibutylboron triflate/diisopropylethylamine. Academic Article uri icon

Overview

abstract

  • [reaction: see text] Dibutylboron triflate/diisopropylethylamine mediated aldol-type cyclization provides an expedient route for the stereoselective synthesis of cyclic ethers in a single step. The method is highly efficient for the stereoselective synthesis of 4-cis-tetrahydropyranones. The reaction is proposed to proceed via an S(N)1-type mechanism through a chair-like transition state, in which both substituents occupy equatorial positions.

publication date

  • January 8, 2004

Identity

Digital Object Identifier (DOI)

  • 10.1021/ol036229b

PubMed ID

  • 14703366

Additional Document Info

volume

  • 6

issue

  • 1