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Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7847-51. doi: 10.1002/anie.201501762. Epub 2015 May 26.

Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter.

Author information

1
Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China).
2
Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). tanb@sustc.edu.cn.
3
Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 (P. R. China). liuxy3@sustc.edu.cn.

Abstract

The first highly enantioselective Brønsted acid catalyzed intramolecular hydroamination of alkenes enables the efficient construction of a series of chiral (spirocyclic) pyrrolidines with an α-tetrasubstituted carbon stereocenter with excellent functional group tolerance. A unique feature of this strategy is the use of a thiourea group acting as both the activating and the directing group through cooperative multiple hydrogen bonding with a Brønsted acid and the double bond. The utility of this method is highlighted by the facile construction of chiral synthetic intermediates and important structural motifs that are widely found in organic synthesis.

KEYWORDS:

Brønsted acid catalysis; alkenes; asymmetric catalysis; hydroamination; pyrrolidines

PMID:
26013971
DOI:
10.1002/anie.201501762
[Indexed for MEDLINE]

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