The catalytic decarboxylative allylation of enol carbonates: the synthesis of enantioenriched 3-allyl-3′-aryl 2-oxindoles and the core structure of azonazine

The catalytic asymmetric synthesis of 3-allyl-3′-aryl 2-oxindoles has been shown via the Pd(0)-catalyzed decarboxylative allylation of allylenol carbonates. This methodology provides access to a variety of 2-oxindole substrates ( 5a-v ) with all-carbon quaternary stereocenters (up to 94% ee) at the...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-12, Vol.2 (1), p.127-131
Main Authors: Babu, K. Naresh, Pal, Souvik, Khatua, Arindam, Roy, Avishek, Bisai, Alakesh
Format: Article
Language:English
Subjects:
Allyl compounds
Aromatic compounds
Asymmetric synthesis
Asymmetry
Carbonates
Chemical reactions
Chemical synthesis
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The catalytic asymmetric synthesis of 3-allyl-3′-aryl 2-oxindoles has been shown via the Pd(0)-catalyzed decarboxylative allylation of allylenol carbonates. This methodology provides access to a variety of 2-oxindole substrates ( 5a-v ) with all-carbon quaternary stereocenters (up to 94% ee) at the pseudobenzylic position under additive-free and mild conditions. The synthetic potential of this method was shown by the asymmetric synthesis of the tetracyclic core of the diketopiparazine-based alkaloid azonazine ( 11 ). Decarboxylative allylation of enol carbonates ( 2 ) afforded 2-oxindoles ( 5 ) in up to 94% ee. This methodology has been utilized for a 3-step construction of tetracyclic core ( 3 ) of azonazine ( 2 ).
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02048j