Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols

The first catalytic regio- and enantioselective aminolysis of 3,4-epoxy alcohols has been accomplished. Under the catalysis of Ni­(ClO4)2·6H2O, the C4 selective ring opening of various 3,4-epoxy alcohols proceeded in a stereospecific manner with high regioselectivities. Furthermore, with the Ni-BINA...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 13; pp. 4308 - 4311
Main Authors Wang, Chuan, Yamamoto, Hisashi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.04.2015
Amer Chemical Soc
Subjects
Alcohols - chemistry
Amines - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Epoxy Compounds - chemistry
Nickel - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
2,3-EPOXY ALCOHOLS
TERMINAL EPOXIDES
EPOXY ALCOHOLS
KINETIC RESOLUTION
HOMOALLYLIC ALCOHOLS
COMPLEXES
ASYMMETRIC EPOXIDATION
SUBSTITUTION-REACTIONS
EFFICIENT
AROMATIC EPOXIDES
Online AccessGet full text

Cover

More Information
Summary:The first catalytic regio- and enantioselective aminolysis of 3,4-epoxy alcohols has been accomplished. Under the catalysis of Ni­(ClO4)2·6H2O, the C4 selective ring opening of various 3,4-epoxy alcohols proceeded in a stereospecific manner with high regioselectivities. Furthermore, with the Ni-BINAM catalytic system the enantioselective ring opening of 3,4-epoxy alcohols furnished various γ-hydroxy-δ-amino alcohols as products with complete regiocontrol and high enantioselectivities (up to 94% ee).
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b01005