Highly stereocontrolled proton transfer in an enammonium-iminium rearrangement. Mechanism of the stereoselective deoxygenation of 6-aryl-6-hydroxy-1,2,3,5,6,10b-hexahydropyrrolo[2.1-]isoquinolines with borane-thf in trifluoroacetic acid.-Reference-Cited by-同舟云学术

Highly stereocontrolled proton transfer in an enammonium-iminium rearrangement. Mechanism of the stereoselective deoxygenation of 6-aryl-6-hydroxy-1,2,3,5,6,10b-hexahydropyrrolo[2.1-]isoquinolines with borane-thf in trifluoroacetic acid.

Published:1988-01 Issue:40 Volume:29 Page:5073-5076
ISSN:0040-4039
Container-title:Tetrahedron Letters
language:en
Short-container-title:Tetrahedron Letters

Author:

Maryanoff Bruce E.,McComsey David F.,Mutter Martin S.,Sorgi Kirk L.,Maryanuff Cynthia A.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference17 articles.

1. Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships

2. McN-5707 and McN-5652-Z

3. Stereochemistry of intramolecular amidoalkylation reactions in the synthesis of polycyclic isoquinoline derivatives

4. Dramatic reversal of diastereoselectivity in an N-acyliminium ion cyclization leading to hexahydropyrrolo[2,1-a]isoquinolines. A case of competing steric interactions

5. Borane complexes in trifluoroacetic acid. Reduction of indoles to indolines and generation of bis(trifluoroacetoxy)borane

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