Stereoselective aldol-type cyclization reaction mediated by dibutylboron triflate/diisopropylethylamine.
[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.
Das
Sanjib
S
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.
Li
Lian-Sheng
LS
Sinha
Subhash C
SC