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Catalytic Asymmetric Aminohydroxylation with Amino‐Substituted Heterocycles as Nitrogen Sources
Author(s) -
Goossen Lukas J.,
Liu Hong,
Dress K. Ruprecht,
Sharpless K. Barry
Publication year - 1999
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/(sici)1521-3773(19990419)38:8<1080::aid-anie1080>3.0.co;2-d
Subject(s) - vicinal , moiety , chemistry , catalysis , osmium , ligand (biochemistry) , yield (engineering) , nitrogen , organic chemistry , amino acid , combinatorial chemistry , ruthenium , receptor , materials science , biochemistry , metallurgy
The suprafacial, vicinal addition of a heterocyclic moiety and a hydroxyl group is achieved by the osmium‐catalyzed asymmetric aminohydroxylation (AA) of olefins with amino‐substituted heterocycles as the nitrogen sources. Amino alcohols are obtained in up to 97 % yield and with up to 99 % ee when a ligand derived from dihydroquinidine (DHQD‐L) is used [Eq. (1); R i indicates the remaining portion of the heterocycle (Het); H 2 O is the O source]. The AA can now be considered as a means to directly introduce complex, biologically relevant substructures to hydrocarbon backbones.