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-HEXAHYDROPYRROLOISOQUINOLINES WITH BORANE-THF IN TRIFLUOROACETIC ACID.

DOI: 10.1016/S0040-4039(00)80682-6

Source and publish data:

Tetrahedron Letters p. 5073 - 5076 (1988)

Update date:2022-08-05

Topics:

Authors:

Maryanoff, Bruce E.

McComsey, David F.

Mutter, Martin S.

Sorgi, Kirk L.

Maryanoff, Cynthia A.

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/S0040-4039(00)80682-6

Either diastereomer of 2 or 10 is deoxygenated with BH3-THF/CF3CO2H to give mainly the trans product, 3b or 11b.The process involes a key enammonium-iminium rearrangement in which there is almost exclusive proton delivery from a single face.

Full text of DOI:10.1016/S0040-4039(00)80682-6

Products guided by the article

Product name:6-(4-(methylthio)phenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline

Cas No:370102-67-3

R&D Labs maybe for 370102-67-3

Huixian Tiankai Paper Making Agent CO.,Ltd.

Contact:+86-373-6899808

Address:Mengdian Industrial Avenue,Huixian,Xinxiang,Henan,China
Sichuan Highlight Fine Chemicals Co., Ltd.

Contact:+86-28-8525 1605

Address:A5-102 Airport base,388 West Airport Huang He Zhong Lu,2 Section
Shandong Topscience Biotech Co., Ltd.

Contact:0633-2619278

Address:No. 98 Lanshan West Road, Lanshan District, Rizhao, Shandong Province, P.R. of China
Wansheng

Contact:86-21-31200601

Address:Room1618,FangzhengDaSha,No.1122 Xinjinqiao Road,Pudong New District,Shanghai ,China
GenicBio Limited

Contact:+86-(0)21-3770 9035

Address:Room 301, Building 2, Meijiabang Road 1508, Shanghai China

Relevant to this article

Doi:10.1039/j39680002537
(1968)
Asymmetric synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives

Doi:10.1021/jo010374q
(2001)
The prins cascade cyclization reaction for the synthesis of angularly-fused tetrahydropyran and piperidine derivatives

Doi:10.1002/ejoc.201201387
(2013)
Sequence-specific DNA interstrand cross-linking by imidazole-pyrrole CPI conjugate

Doi:10.1021/ja003660c
(2001)
2,6-Dipyrazinylpyridines and their ruthenium(II) complexes: A new polynucleating ligand family

Doi:10.1021/ic015545o
(2001)
Syntheses and characterization of aluminium(III), iron(III), and copper(II) monobromoacetates and their complexes with organic bases

Doi:10.1081/SIM-100105262
(2001)

Article Doi