Traceless Redox-Annulations of Alicyclic Amines-Reference-Cited by-同舟云学术

Traceless Redox-Annulations of Alicyclic Amines

Published:2020-10 Issue:04 Volume:04 Page:123-131
ISSN:2509-9396
Container-title:SynOpen
language:en
Short-container-title:SynOpen

Author:

Rickertsen Dillon R. L.¹,Ma Longle²^ORCID,Seidel Daniel¹^ORCID,Paul Anirudra¹,Abboud Khalil A.³

Affiliation:

1. Center for Heterocyclic Compounds, Department of Chemistry, University of Florida

2. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey

3. Center for X-ray Crystallography, Department of Chemistry, University of Florida

Abstract

AbstractAmines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C–H bond and N–H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid.

Funder

National Institute of General Medical Sciences

National Science Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Materials Science (miscellaneous),Biomaterials,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1706004.pdf

Reference3 articles.

1. Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes

2. Pd-Catalyzed Cleavage of Benzylic Nitro Bonds: New Opportunities for Asymmetric Synthesis