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Literature DB >> 22263967

A stereoselective hydroamination transform to access polysubstituted indolizidines.

Sergey V Pronin¹, M Greg Tabor, Daniel J Jansen, Ryan A Shenvi.

Abstract

Stereoselective, intramolecular, formal hydroamination of dienamines via directed hydroboration is reported. Four stereocenters are set in the process. Natural and unnatural indolizidine alkaloids can be synthesized from simple unsaturated amines using the title process.

Entities: Chemical

Mesh：

Substances：
Indolizidines
Polymers

Year: 2012 PMID： 22263967 DOI： 10.1021/ja211090n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

11 in total

1. Alkaloid synthesis: indolizidines with ease.

Authors: Peter Shapland
Journal: Nat Chem Date: 2012-05-22 Impact factor: 24.427

2. Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Authors: Hongze Li; Shou-Jie Shen; Cheng-Liang Zhu; Hao Xu
Journal: J Am Chem Soc Date: 2019-05-30 Impact factor: 15.419

3. Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors: Qilei Zhu; David E Graff; Robert R Knowles
Journal: J Am Chem Soc Date: 2018-01-04 Impact factor: 15.419

A stereoselective hydroamination transform to access polysubstituted indolizidines.

1. Alkaloid synthesis: indolizidines with ease.

2. Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

3. Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

4. Isomerization of N-Allyl Amides To Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides.

5. Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

6. Intramolecular C(sp3)-N coupling by oxidation of benzylic C,N-dianions.

7. Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

8. Direct stereospecific amination of alkyl and aryl pinacol boronates.

9. Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

10. Total synthesis of alkaloid 205B.