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Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael-Hemiacetalization Reaction.

ABSTRACT: Starting from ?-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).

SUBMITTER: Urbanietz G

PROVIDER: S-EPMC4181541 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael-Hemiacetalization Reaction.

Urbanietz Gregor G Atodiresei Iuliana I Enders Dieter D

Synthesis 20140501 9

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). ...[more]

PMID: 25284900

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