Diastereoselective construction of spirocyclic pyrrolidines bearing two quaternary centers via Cu-II-P, N-Ligand catalyzed 1,3-dipolar cycloaddition

Here, we report a convenient access to diastereoselective synthesis of polysubstituted pyrrolidines bearing a unique Spiro quaternary center at the C-2 position and another quaternary center at C-4. The synthesis system, (CuP)-P-II/, N-Ligand-catalyzed 1, 3-dipolar cycloaddition, by employing homose...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 7; pp. 923 - 930
Main Authors Tang, Li-Wei, Li, Chuan, Zhao, Bao-Jing, Lan, Li, Zhang, Man, Zhou, Zhi-Ming
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 16.02.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,3-Dipolar cycloaddition
ASYMMETRIC CONSTRUCTION
Quaternary center
ENANTIOSELECTIVE SYNTHESIS
Spirolactone
DRUG DISCOVERY
AZOMETHINE YLIDES
ZH COMPOUNDS
POTENTIAL 1,3-DIPOLES
Spiropyrrolidine
DIVERSITY-ORIENTED SYNTHESIS
STEREOSELECTIVE CONSTRUCTION
CARBON STEREOCENTERS
EFFICIENT CONSTRUCTION
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Summary:Here, we report a convenient access to diastereoselective synthesis of polysubstituted pyrrolidines bearing a unique Spiro quaternary center at the C-2 position and another quaternary center at C-4. The synthesis system, (CuP)-P-II/, N-Ligand-catalyzed 1, 3-dipolar cycloaddition, by employing homoserine lactone derived cyclic imino esters as the dipoles and alpha, alpha,beta-trisubstituted olefins as the dipolarophlies, provides exo-spiro-pyrrolidines with good yields, high diastereoselectivities (up to >98:2 dr) and performs well for a broad scope of substrates. (C) 2017 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2017.01.001