Enantio- and Diastereoselective Synthesis of Piperidines by Coupling of Four Components in a “One-Pot” Sequence Involving Diphenylprolinol Silyl Ether Mediated Michael Reaction
Tatsuya Urushima
Daisuke Sakamoto
Hayato Ishikawa
Yujiro Hayashi
10.1021/ol1018932.s001
https://acs.figshare.com/articles/journal_contribution/Enantio_and_Diastereoselective_Synthesis_of_Piperidines_by_Coupling_of_Four_Components_in_a_One_Pot_Sequence_Involving_Diphenylprolinol_Silyl_Ether_Mediated_Michael_Reaction/2721796
An efficient, asymmetric, four-component, one-pot synthesis of highly substituted piperidines with excellent diastereo- and enantioselectivity was established through the diphenylprolinol silyl ether mediated Michael reaction of aldehyde and nitroalkene, followed by the domino aza-Henry reaction/hemiaminalization reaction and a Lewis acid mediated allylation or cyanation reaction. All carbons of the piperidine ring are substituted with different groups, and its five contiguous stereocenters are completely controlled in both relative and absolute senses.
2010-10-15 00:00:00
Lewis acid
Diphenylprolinol Silyl Ether Mediated Michael Reaction
Diastereoselective Synthesis
piperidine ring
diphenylprolinol silyl ether
cyanation reaction
Michael reaction