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Highly stereoselective synthesis of 2,6- cis -substituted tetrahydropyrans using a one-pot sequential catalysis
Q. Dai, , J.C.-G. Zhao
Published in
Volume: 15
Issue: 12
Pages: 2922 - 2925
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. © 2013 American Chemical Society.
About the journal
JournalOrganic Letters