4.4 Article

Asymmetric aminoarylation for the synthesis of trans-3-amino-4-aryltetrahydroquinolines: An access to aza-analogue of dihydrexidine

Journal

TETRAHEDRON
Volume 103, Issue -, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132257

Keywords

Tetrahydroquinoline; Asymmetric reaction; Aminoarylation; Aziridine; Friedel-crafts reaction

Funding

  1. SERB, India [SR/S1/OC-97/2012, CRG/2020/000650]

Ask authors/readers for more resources

A proficient stereoselective aminoarylation reaction of N-cinnamylanilines was developed based on a two-step protocol involving catalytic enantioselective aziridination and subsequent 6-endo-tet Friedel-Crafts cyclization. The reaction showed excellent diastereo- and enantioselectivity in the synthesis of trans-3-amino-4-aryltetrahydroquinolines, with the potential for concise synthesis of bioactive compounds.
A proficient stereoselective aminoarylation reaction of N-cinnamylanilines, based on a two-step protocol of catalytic enantioselective aziridination and subsequent 6-endo-tet Friedel-Crafts cyclization, has been developed and demonstrated. A pair of chiral bis-oxazoline ligand and Cu(OTf)(2) offered an effective combination in the synthesis of trans-3-amino-4-aryltetrahydroquinolines with excellent diastereo- and enantioselectivity (dr: >99: 1 and ee up to 97%). In continuation, a trans-3-amino-4-aryltetrahydroquinoline, availed in one-pot stereoselective aminoarylation reaction, was extended toward a concise synthesis of aza-analogue of dihydrexdine, a potent and selective full dopamine-D1 agonist. (C) 2021 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.4
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available