Synthesis of spirooxindoles<i>via</i>formal acetylene insertion into a common palladacycle intermediate-Reference-Cited by-同舟云学术

Synthesis of spirooxindolesviaformal acetylene insertion into a common palladacycle intermediate

Published:2023 Issue:21 Volume:14 Page:5650-5655
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Abel-Snape Xavier¹^ORCID,Johnson Colton E.¹^ORCID,Imbriaco Bianca¹^ORCID,Lautens Mark¹^ORCID

Affiliation:

1. Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S 3H6, Canada

Abstract

A palladium-catalyzed spirocyclization reaction is reported and proposed to ariseviadiastereoselective insertion of an oxabicycle into a palladacycle. The cycloadduct undergoes a post-catalytic retro-Diels–Alder step to furnish a previously inaccessiblecis-alkene.

Funder

Natural Sciences and Engineering Research Council of Canada

Kennarshore

University of Toronto

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/SC/D3SC01072D

Reference50 articles.

1. Aryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation