A stereoselective hydroamination transform to access polysubstituted indolizidines

Sergey V Pronin; M Greg Tabor; Daniel J Jansen; Ryan A Shenvi

doi:10.1021/ja211090n

A stereoselective hydroamination transform to access polysubstituted indolizidines

J Am Chem Soc. 2012 Feb 1;134(4):2012-5. doi: 10.1021/ja211090n. Epub 2012 Jan 20.

Authors

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

Affiliation

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 22263967
DOI: 10.1021/ja211090n

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Crystallography, X-Ray
Indolizidines / chemical synthesis*
Indolizidines / chemistry
Models, Molecular
Molecular Conformation
Polymers / chemical synthesis*
Polymers / chemistry
Stereoisomerism

Substances

Indolizidines
Polymers