1443014-09-2Relevant academic research and scientific papers
Highly stereoselective synthesis of 2,6- cis -substituted tetrahydropyrans using a one-pot sequential catalysis
Dai, Qipu,Rana, Nirmal K.,Zhao, John Cong-Gui
supporting information, p. 2922 - 2925 (2013/07/26)
A catalytic highly diastereo- and enantioselective synthesis of 2,6-cis-substituted tetrahydropyrans was realized using a one-pot sequential catalysis involving Henry and oxa-Michael reactions. The nitroaldol products obtained in a highly enantioselective copper(II)-catalyzed Henry reaction between nitromethane and 7-oxo-hept-5-enals were subsequently treated with a catalytic amount of camphorsulfonic acid (CSA) to give the desired tetrahydropyran derivatives in excellent yields, diastereoselectivities (dr >99:1), and enantioselectivities (ee = 98-99%). The reaction can also be used for the high stereoselective synthesis of a cis-2,6-disubstituted morpholine.
