Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols |
| |
Authors: | Hodgson David M Stent Matthew A H Stefane Bogdan Wilson Francis X |
| |
Institution: | Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK. david.hodgson@chem.ox.ac.uk |
| |
Abstract: | A screen of external chiral ligands has led to enantioselective organolithium-induced alkylative double ring-opening of 3,4-epoxytetrahydrofuran 1 with n-BuLi to give 3-methyleneheptane-1,2-diol 3 in 75% yield and 55% ee in the presence of bisoxazoline 10, and in up to 60% ee in the presence of (-)-sparteine 2. Extending the alkylative double ring-opening reaction to epoxides derived from oxabicyclon.2.1]alkenes (n = 2.3) results in the formation of cycloalkenediols, which, when carried out in the presence of (-)-sparteine 2 affords products in up to 85% ee. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|