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Literature DB >> 35972395

Synthesis of Tertiary Amines through Extrusive Alkylation of Carbamates.

Guoliang Zhang¹, David Favela¹, Winston L Chow¹, Rishab N Iyer¹, Alexander J Pell¹, David E Olson^1,2,3.

Abstract

Basic amines are key elements of many biologically active natural products and pharmaceuticals. Given their inherent reactivity, it is often necessary to protect basic amines during target-directed synthesis, which results in wasteful protection/deprotection sequences. We report a step-economical approach enabling the protection of secondary amines as carbamates prior to their conversion to tertiary amines via the formal extrusion of CO2. This method is applied to the synthesis of iboga alkaloids (±)-conodusine A and (±)-conodusine B.

Entities: Chemical

Mesh：

Substances：
Amines
Carbamates

Year: 2022 PMID： 35972395 PMCID： PMC9420822 DOI： 10.1021/acs.orglett.2c02516

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.072

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References

23 in total

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Authors: Choy-Eng Nge; Kam-Weng Chong; Noel F Thomas; Siew-Huah Lim; Yun-Yee Low; Toh-Seok Kam
Journal: J Nat Prod Date: 2016-04-14 Impact factor: 4.050

Synthesis of Tertiary Amines through Extrusive Alkylation of Carbamates.

1. Constructing Iboga alkaloids via C-H bond functionalization: examination of the direct and catalytic union of heteroarenes and isoquinuclidine alkenes.

2. Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene.

3. N,N'-carbonyldiimidazole-mediated cyclization of amino alcohols to substituted azetidines and other N-heterocycles.

4. General and highly efficient synthesis of 2-alkylideneazetidines and beta-lactams via copper-catalyzed intramolecular N-vinylation.

5. Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution.

6. Skeletal editing through direct nitrogen deletion of secondary amines.

Review 7. Organic carbamates in drug design and medicinal chemistry.

8. Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines.

9. Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.