Catalytic asymmetric aminohydroxylation with amino-substituted heterocycles as nitrogen sources

L J Goossen; H Liu; K R Dress; K B Sharpless

doi:10.1002/(SICI)1521-3773(19990419)38:8<1080::AID-ANIE1080>3.0.CO;2-D

Catalytic asymmetric aminohydroxylation with amino-substituted heterocycles as nitrogen sources

Angew Chem Int Ed Engl. 1999;38(8):1080-3. doi: 10.1002/(SICI)1521-3773(19990419)38:8<1080::AID-ANIE1080>3.0.CO;2-D.

Authors

L J Goossen¹, H Liu, K R Dress, K B Sharpless

Affiliation

¹ Department of Chemistry (and) The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-784-7562.

Abstract

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); H2 O is the O source]. The AA can now be considered as a means to directly introduce complex, biologically relevant substructures to hydrocarbon backbones.

Keywords: Amino alcohols; Aminohydroxylations; Asymmetric synthesis; Heterocycles; Homogeneous catalysis.