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Diastereoselective rearomative etherifications and aminations of 2,3,9,9a-tetrahydro-1H-carbazoles

DOI: 10.1016/j.tet.2021.132144 DOI Help

Authors: Matokah M. Abualnaja (Newcastle University; Umm Al-Qura University) , Joseph Cowell (Newcastle University) , John D. Jolliffe (Newcastle University) , Corinne Wills (Newcastle University) , Paul G. Waddell (Newcastle University) , William Clegg (Newcastle University) , Michael J. Hall (Newcastle University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Tetrahedron , VOL 89 , PAGES 132144

State: Published (Approved)
Published: April 2021
Diamond Proposal Number(s): 8682

Abstract: Herein we present a rearomative diastereoselective etherification/amination reaction of 2,3,9,9a-tetrahydro- 1H-carbazoles, themselves accessible via the Diels-Alder reaction of N-protected 3-vinyl-1H-indoles. We have developed a one-pot rearomative bromination/nucleophilic substitution reaction sequence employing both O- and N-centred nucleophiles, inverting the typical reactivity of 2,3,9,9a-tetrahydro-1H-carbazoles at the 4-position. Alcohols or secondary amines can be incorporated allowing access to the corresponding 4-substituted- 2,3,4,9-tetrahydro-1H-carbazoles, the diastereoselectivity of the reaction being controlled by the nature of the nucleophile and the reaction conditions.

Journal Keywords: Carbazole; One-pot reaction; Diastereocontrol; Substitution reaction; Bromination

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Discipline Tags:

Organic Chemistry Chemistry

Technical Tags:

Diffraction Small Molecule Diffraction