Beilstein J. Org. Chem.2020,16, 2073–2079, doi:10.3762/bjoc.16.174
University, Leninskie Gory, 1, 119991, Mosсow, Russian Federation 10.3762/bjoc.16.174 Abstract A new synthetic strategy toward nonracemic phosphoryl-substituted pyrrolidines and tetrahydropyranes with three and five contiguous stereocenters is presented. Readily available β-keto phosphonates react with
; tetrahydropyranes; Introduction
Сhiral phosphonates [1][2] and phosphoryl-substituted heterocycles [2][3][4] have received significant attention in recent years due to their wide range of biological activity. For example, SF-2312 (1) is a natural antibiotic – an enolase inhibitor produced by the actinomycete
heterocycles. The present work reports on the synthesis of nonracemic phosphoryl-substituted pyrrolidines and tetrahydropyranes via Ni(II)-catalyzed asymmetric Michael addition of β-keto phosphonates to conjugated nitroolefins.
Results and Discussion
For the synthesis of nonracemic polysubstituted pyrrolidin-3
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Graphical Abstract
Figure 1:
Pharmacologically active nonracemic phosphonates with heterocyclic moieties.
Beilstein J. Org. Chem.2015,11, 31–36, doi:10.3762/bjoc.11.5
alkenols with CBr4 as the bromine source, utilizing visible-light-induced phototedox catalysis. The reaction proceeds with high efficiency and regioselectivity for the synthesis of β-bromotetrahydrofurans and -tetrahydropyranes.
Experimental
General procedure for the photocatalytic bromoetherification of
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Graphical Abstract
Scheme 1:
Control experiment with liquid bromine for bromoethrification of alkenols.