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

Authors
Park, Jong-UnAhn, Hye-InCho, Ho-JunXuan, ZiKim, Ju Hyun
Issue Date
27-Apr-2020
Publisher
WILEY-V C H VERLAG GMBH
Keywords
Oxazolidines; Cycloaddition; Asymmetric catalysis; Sulfamidates; Quaternary stereocenter
Citation
ADVANCED SYNTHESIS & CATALYSIS, v.362, no.9, pp 1836 - 1840
Pages
5
Indexed
SCIE
SCOPUS
Journal Title
ADVANCED SYNTHESIS & CATALYSIS
Volume
362
Number
9
Start Page
1836
End Page
1840
URI
https://scholarworks.gnu.ac.kr/handle/sw.gnu/6705
DOI
10.1002/adsc.201901497
ISSN
1615-4150
1615-4169
Abstract
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.
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