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. 2014 May 1;46(9):1261-1269.
doi: 10.1055/s-0033-1340826.

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

Gregor Urbanietz  1 , Iuliana Atodiresei  1 , Dieter Enders  1
Affiliations

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

Gregor Urbanietz et al. Synthesis (Stuttg). .

Abstract

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).

Keywords: domino reaction; hydrogen bonding; one-pot reaction; organocatalysis; tetrahydropyrans.

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Figures

Figure 1
Figure 1
Absolute configuration of trans-3g confirmed by X-ray crystal-structure analysis
Scheme 1
Scheme 1
Domino Michael–hemiacetalization reactions towards chromanols 6 or tetrahydropyranols 3 and dihydropyrans 4
Scheme 2
Scheme 2
Various synthetic transformations of enantiopure tetrahydropyranol trans-3a
See this image and copyright information in PMC

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