Starting from α-hydroxymethyl nitroalkenes and various 1,3-dicarbonyl compounds, a one-pot organocatalyzed diastereo- and enantioselective synthesis of polyfunctionalized dihydro- and tetrahydropyran derivatives via a domino Michael-hemiacetalization sequence is reported. The title compounds bearing a variety of functional groups can be synthesized in this way in good yields (59-91%) and with moderate to excellent diastereoselectivities (26-98% de) and enantioselectivities (71-99% ee).
Starting from α-hydroxymethyl nitroalkenes and various n class="Chemical">1,3-dicarbonyl compounds, a one-pot organocatalyzed diastereo- and enantioselective synthesis of polyfunctionalized dihydro- and tetrahydropyran derivatives via a domino Michael-hemiacetalization sequence is reported. The title compounds bearing a variety of functional groups can be synthesized in this way in good yields (59-91%) and with moderate to excellent diastereoselectivities (26-98% de) and enantioselectivities (71-99% ee).
Authors: Diego A Alonso; Alejandro Baeza; Rafael Chinchilla; Cecilia Gómez; Gabriela Guillena; Isidro M Pastor; Diego J Ramón Journal: Molecules Date: 2017-05-29 Impact factor: 4.411
Authors: Alexander N Reznikov; Dmitry S Nikerov; Anastasiya E Sibiryakova; Victor B Rybakov; Evgeniy V Golovin; Yuri N Klimochkin Journal: Beilstein J Org Chem Date: 2020-08-25 Impact factor: 2.883