Chiral Monofluorobenzyl Carbanions: Synthesis of Enantiopure β-Fluorinated β-Phenylethylamines

The preparation of a stabilized monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N‐p‐tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, wh...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2011-05, Vol.17 (22), p.6142-6147
Main Authors: García Ruano, José L., Parra, Alejandro, Alonso, Inés, Fustero, Santos, del Pozo, Carlos, Arroyo, Yolanda, Sanz-Tejedor, Ascensión
Format: Article
Language:English
Subjects:
Anions - chemistry
asymmetric synthesis
Benzyl Compounds - chemistry
fluorinated carbanions
Halogenation
Imines - chemistry
ionic liquids
Molecular Conformation
Phenethylamines - chemical synthesis
Phenethylamines - chemistry
Stereoisomerism
stereoselectivity
sulfinylimines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The preparation of a stabilized monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N‐p‐tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure β‐fluorinated β‐phenylethylamines. A monofluorobenzyl carbanion can be stabilized by remote homochiral sulfinyl groups and reacts with N‐sulfinylaldimines in a completely stereoselective manner (see scheme). Chiral auxiliaries can be removed with tBuLi without epimerization at the benzylic position. These reactions open a general route for preparing enantiomerically pure benzyl fluorides.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201100455