Enantioselective Synthesis of syn- and anti-1,3-Aminoalcohols via β-Aminoketones and Subsequent Reduction/Dynamic Kinetic Asymmetric Transformation
- 13 October 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (43) , 15182-15184
- https://doi.org/10.1021/ja107857v
Abstract
β-Aminoketones obtained from imines in an organocatalytic Mannich reaction were transformed to enantio- and diastereomerically pure 1,3-aminoalcohols with two stereogenic centers via a combined reduction/dynamic kinetic asymmetric transformation. Both syn and anti diastereomers were obtained in high yield, dr, and ee.This publication has 26 references indexed in Scilit:
- Asymmetric Synthesis of Acyclic 1,3-Amino Alcohols by Reduction of N-Sulfinyl β-Amino Ketones. Formal Synthesis of (−)-Pinidinol and (+)- EpipinidinolThe Journal of Organic Chemistry, 2008
- 1,3-Aminoalcohols and Their Derivatives in Asymmetric Organic SynthesisChemical Reviews, 2007
- Epoxyalcohol route to hydroxyethylene dipeptide isosteres: a new synthesis of the diaminoalcohol core of HIV-protease inhibitor ABT-538 (Ritonavir)Chemical Communications, 2001
- Synthesis of a potent wide-spectrum serotonin-, norepinephrine-, dopamine-reuptake inhibitor (SNDRI) and a species-selective dopamine-reuptake inhibitor based on the gamma-amino alcohol functional groupBioorganic & Medicinal Chemistry Letters, 1998
- Dysiherbaine: A New Neurotoxic Amino Acid from the Micronesian Marine Sponge Dysidea herbaceaJournal of the American Chemical Society, 1997
- Synthesis of Complex Nucleoside AntibioticsChemical Reviews, 1995
- Stereoselective synthesis of sperabillins and related compoundsJournal of the Chemical Society, Perkin Transactions 1, 1991
- Stereocontrolled synthesis of (+)-negamycin from an acyclic homoallylamine by 1,3-asymmetric inductionJournal of the American Chemical Society, 1982
- Intramolecular nitrile oxide cycloaddition (INOC) reactions in the indole series. 2. Total synthesis of racemic and optically active paliclavine and 5-epi-paliclavineThe Journal of Organic Chemistry, 1981
- Total syntheses of negamycin and the antipodeJournal of the American Chemical Society, 1972