DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Nucleophilic ring opening of trans -2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

Journal Article · · ChemComm
DOI: https://doi.org/10.1039/C8CC07200K · OSTI ID:1480555

We report the nucleophilic ring opening of unsymmetrical trans -epoxides to β-amino alcohols with catalyst-controlled regioselectivity.

Sponsoring Organization:
USDOE
Grant/Contract Number:
FG02-05ER15687
OSTI ID:
1480555
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 92 Vol. 54; ISSN CHCOFS; ISSN 1359-7345
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English

References (38)

Catalytic Asymmetric Aminohydroxylation with Amino-Substituted Heterocycles as Nitrogen Sources journal April 1999
Laccase-Mediated Deprotection ofpara-Methoxyphenyl (PMP)-Protected Amines journal June 2007
Regiodivergent Epoxide Opening: A Concept in Stereoselective Catalysis beyond Classical Kinetic Resolutions and Desymmetrizations journal October 2007
Ring-Opening of Epoxides in Water journal March 2011
Regiochemical control of the ring opening of 1:2-epoxides by means of chelating processes. 10. Synthesis and ring opening reactions of mono- and difunctionalized cis and trans aliphatic oxirane systems journal September 1995
Metal complexes of chiral binaphthyl Schiff-base ligands and their application in stereoselective organic transformations journal July 2003
Stereocontrolled ‘one pot’ organometallic addition–ring opening reaction of α,β-aziridine aldehydes. A new entry to syn 1,2-amino alcohols journal December 2001
Unusual reactivity of selenoboranes towards epoxides: new selective routes to b-hydroxyselenides and allylalcohols journal January 1981
Solution-phase synthesis of a β-amino alcohol combinatorial library journal June 1997
Amino alcohol-mediated enantioselective syntheses of α-substituted indanones and tetralones, ammonium enolates as key intermediates journal May 2014
Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group journal November 2006
Metal-Catalyzed Directed Regio- and Enantioselective Ring-Opening of Epoxides journal January 2016
Asymmetric Catalysis of Epoxide Ring-Opening Reactions journal June 2000
1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis journal January 1996
Three-Dimensional {Co 3+ –Zn 2+ } and {Co 3+ –Cd 2+ } Networks Originated from Carboxylate-rich Building Blocks: Syntheses, Structures, and Heterogeneous Catalysis journal September 2013
Highly Enantioselective Ring Opening of Epoxides Catalyzed by (salen)Cr(III) Complexes journal May 1995
The Development of Scalemic Multidentate Niobium Complexes as Catalysts for the Highly Stereoselective Ring Opening of meso -Epoxides and meso -Aziridines journal July 2007
Regioselective Carbonylation of trans -Disubstituted Epoxides to β-Lactones: A Viable Entry into syn -Aldol-Type Products journal July 2013
Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides journal May 2014
Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols journal March 2015
Regioselective Isomerization of 2,3-Disubstituted Epoxides to Ketones: An Alternative to the Wacker Oxidation of Internal Alkenes journal November 2015
Organotin phosphate condensates as a catalyst of selective ring-opening of oxiranes by alcohols journal January 1988
Efficient N-p -Methoxyphenyl Amine Deprotection through Anodic Oxidation journal December 2005
Zinc(II) Perchlorate Hexahydrate Catalyzed Opening of Epoxide Ring by Amines:  Applications to Synthesis of ( RS )/( R )-Propranolols and ( RS )/( R )/( S )-Naftopidils journal May 2007
Carbonylation of cis -Disubstituted Epoxides to trans -β-Lactones: Catalysts Displaying Steric and Contrasteric Regioselectivity journal October 2014
Isolation and Structure Determination of Obyanamide, a Novel Cytotoxic Cyclic Depsipeptide from the Marine Cyanobacterium Lyngbya confervoides journal January 2002
New Supported β-Amino Alcohols as Efficient Catalysts for the Enantioselective Addition of Diethylzinc to Benzaldehyde under Flow Conditions journal October 2002
The C2 Selective Nucleophilic Substitution Reactions of 2,3-Epoxy Alcohols Mediated by Trialkyl Borates:  The First endo -Mode Epoxide-Opening Reaction through an Intramolecular Metal Chelate journal May 2003
O -Nucleophilic Amino Alcohol Acyl-Transfer Catalysts:  the Effect of Acidity of the Hydroxyl Group on the Activity of the Catalyst journal October 2003
Lithium Amide Assisted Asymmetric Mannich-Type Reactions of Menthyl Acetate with PMP-Aldimines journal May 2004
Unravelling a New Class of Chiral Organocatalyst for Asymmetric Ring-Opening Reaction of Meso Epoxides with Anilines journal May 2014
Tungsten-, Molybdenum-, and Cerium-Promoted Regioselective and Stereospecific Halogenation of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides journal November 2014
Synthesis of (+)- and (−)-Monanchorin journal February 2009
Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-β-lactones: effect of salen-ligand electronic variation on enantioselectivity journal January 2014
Lanthanide-based coordination polymers as promising heterogeneous catalysts for ring-opening reactions journal January 2016
Enantioenriched β-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides journal January 2014
Regioselective Ring Opening of Enantiomerically Enriched Epoxides via Catalysis with Chiral (Salen)Cr(III) Complexes journal January 2001
Recent trends in ring opening of epoxides by amines as nucleophiles journal February 2016