title: Stereoselective aldol-type cyclization reaction mediated by dibutylboron triflate/diisopropylethylamine.
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.
authors.affiliation: The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Sanjib
authors.initials: S
authors.lastname: Das
authors.forename: Lian-Sheng
authors.initials: LS
authors.lastname: Li
authors.forename: Subhash C
authors.initials: SC
authors.lastname: Sinha