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One-pot tandem diastereoselective and enantioselective synthesis of functionalized oxindole-fused spiropyrazolidine frameworks.

Authors
Type
Published Article
Journal
Chemistry - A European Journal
1521-3765
Publisher
Wiley Blackwell (John Wiley & Sons)
Publication Date
Volume
20
Issue
41
Pages
13136–13142
Identifiers
DOI: 10.1002/chem.201403990
PMID: 25169758
Source
Medline
Keywords
  • Ligands
  • Oxindoles
  • Palladium
  • Pyrazolidines
  • Tandem Reactions

Abstract

A highly efficient palladium(0)-catalyzed asymmetric [3+2] cycloaddition using 3-diazooxindoles serving as dipolarophiles affords functionalized pyrazolidine derivatives in an atom-economical way. In addition, by trapping the pyrazolidine derivatives with maleimides, the corresponding spiropyrazolidine oxindoles containing multiple stereogenic centers have been obtained in high yields along with moderate to good levels of diastereoselectivity and enantioselectivity under mild conditions. Thus, a novel three-component one-pot tandem reaction has been developed.

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