Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2 H -pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction.
| Autor: | Reznikov AN; Department of Organic Chemistry, Samara State Technical University, Molodogvardeyskaya str., 244, 443100 Samara, Russian Federation., Nikerov DS; Department of Organic Chemistry, Samara State Technical University, Molodogvardeyskaya str., 244, 443100 Samara, Russian Federation., Sibiryakova AE; Department of Organic Chemistry, Samara State Technical University, Molodogvardeyskaya str., 244, 443100 Samara, Russian Federation., Rybakov VB; Department of Chemistry, Moscow State University, Leninskie Gory, 1, 119991, Mosсow, Russian Federation., Golovin EV; Department of Organic Chemistry, Samara State Technical University, Molodogvardeyskaya str., 244, 443100 Samara, Russian Federation., Klimochkin YN; Department of Organic Chemistry, Samara State Technical University, Molodogvardeyskaya str., 244, 443100 Samara, Russian Federation. |
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| Jazyk: | angličtina |
| Zdroj: | Beilstein journal of organic chemistry [Beilstein J Org Chem] 2020 Aug 25; Vol. 16, pp. 2073-2079. Date of Electronic Publication: 2020 Aug 25 (Print Publication: 2020). |
| DOI: | 10.3762/bjoc.16.174 |
| Abstrakt: | 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 conjugated nitroolefins in the presence of a chiral Ni(II) complex to give nitro keto phosphonates with two stereocenters with excellent enantioselectivity and moderate to high diastereoselectivity. These products were used for a reductive cyclization leading to pyrrolidin-3-ylphosphonic acid and for reactions with aldehydes yielding tetrahydropyranylphosphonates as individual stereoisomers. These nonracemic heterocycles containing phosphoryl moieties are useful for designing new pharmacologically active compounds. (Copyright © 2020, Reznikov et al.; licensee Beilstein-Institut.) |
| Databáze: | MEDLINE |
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