Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids
Authors:
- 8 February 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (5) , 1748-1751
Abstract
Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.Keywords
This publication has 30 references indexed in Scilit:
- Synthesis of all stereoisomers of 3-hydroxypipecolic acid and 3-hydroxy-4,5-dehydropipecolic acid and their evaluation as glycosidase inhibitorsBioorganic & Medicinal Chemistry Letters, 2008
- Rhodium-Catalyzed Cyclohydrocarbonylation Approach to the Syntheses of Enantiopure HomokainoidsThe Journal of Organic Chemistry, 2007
- Amidocarbonylation, Cyclohydrocarbonylation, and Related Reactions2007
- Recent advances in cyclohydrocarbonylation reactionsCanadian Journal of Chemistry, 2005
- General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and SwainsonineThe Journal of Organic Chemistry, 2005
- Iminosugar Glycosidase Inhibitors: Structural and Thermodynamic Dissection of the Binding of Isofagomine and 1-Deoxynojirimycin to β-GlucosidasesJournal of the American Chemical Society, 2003
- Rhodium-Catalyzed Cyclohydrocarbonylation: Application to the Synthesis of (+)-Prosopinine and (−)-DeoxoprosophyllineThe Journal of Organic Chemistry, 1998
- New and Efficient Route to Pipecolic Acid Derivatives by Means of Rh-Catalyzed Intramolecular CyclohydrocarbonylationThe Journal of Organic Chemistry, 1995
- The synthesis and configurational stability of differentially protected .beta.-hydroxy-.alpha.-amino aldehydesThe Journal of Organic Chemistry, 1987
- Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditionsThe Journal of Organic Chemistry, 1987