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Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter
Author(s) -
Lin JinShun,
Yu Peng,
Huang Lin,
Zhang Pan,
Tan Bin,
Liu XinYuan
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501762
Subject(s) - stereocenter , hydroamination , brønsted–lowry acid–base theory , enantioselective synthesis , chemistry , intramolecular force , catalysis , functional group , combinatorial chemistry , hydrogen bond , thiourea , organocatalysis , organic chemistry , molecule , polymer
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.