Asymmetric Synthesis of N‐Fused 1,3‐Oxazolidines via Pd‐Catalyzed Decarboxylative (3+2) Cycloaddition

Efficient synthesis of optically active N‐fused 1,3‐oxazolidines containing quaternary and tertiary stereocenters was achieved via Pd‐catalyzed asymmetric (3+2) cycloadditions of sulfamate‐derived cyclic imines and vinylethylene carbonates. Using a chiral phosphoramidite ligand, the cycloadditions p...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 362; no. 9; pp. 1836 - 1840
Main Authors Park, Jong‐Un, Ahn, Hye‐In, Cho, Ho‐Jun, Xuan, Zi, Kim, Ju Hyun
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 27.04.2020
Wiley Subscription Services, Inc
Subjects
Asymmetric catalysis
Asymmetry
Carbonates
Chemistry
Chemistry, Applied
Chemistry, Organic
Cycloaddition
Imines
Optical activity
Oxazolidine
Oxazolidines
Palladium
Physical Sciences
Quaternary stereocenter
Science & Technology
Sulfamidates
TRANS-PERHYDROINDOLIC ACID
Cycloaddition
SULFONYLIMINES
Oxazolidines
VINYLETHYLENE CARBONATES
IMINES
Sulfamidates
Quaternary stereocenter
Asymmetric catalysis
ENANTIOSELECTIVE CONSTRUCTION
Online AccessGet full text

Cover

More Information
Summary:Efficient synthesis of optically active N‐fused 1,3‐oxazolidines containing quaternary and tertiary stereocenters was achieved via Pd‐catalyzed asymmetric (3+2) cycloadditions of sulfamate‐derived cyclic imines and vinylethylene carbonates. Using a chiral phosphoramidite ligand, the cycloadditions proceeded effectively providing sulfamidate‐fused 1,3‐oxazolidines in high yields (up to 96%) with stereoselectivities (up to 25:1 dr; >99% ee). Additionally, the scale‐up reaction and further transformations of the product were also achieved demonstrating the synthetic utility toward the construction of useful heterocycles such as chiral oxazoline bearing a quaternary stereocenter.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901497