Palladium-Catalyzed Regio- and Stereoselective Formate Reduction of Fluorine-Containing Allylic Mesylates. A New Entry for the Construction of a Tertiary Carbon Attached with a Fluoroalkyl Group

Palladium-Catalyzed Regio- and Stereoselective Formate Reduction of Fluorine-Containing Allylic Mesylates. A New Entry for the Construction of a Tertiary Carbon Attached with a Fluoroalkyl Group

The regioselective palladium-catalyzed formate reduction of γ-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the γ position, the corresponding reduction products with a fluo...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry Vol. 71; no. 9; pp. 3545 - 3550
Main Authors: Konno, Tsutomu, Takehana, Tsuyoshi, Mishima, Makoto, Ishihara, Takashi
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 28-04-2006
Subjects:
Allyl Compounds - chemistry
Catalysis
Chemistry
Exact sciences and technology
Formates - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Mesylates - chemistry
Organic chemistry
Oxidation-Reduction
Palladium - chemistry
Stereoisomerism
Catalytic reaction
Transition element complexes
Regioselectivity
Organic phosphine
Palladium complex
Chiral compound
Allylic compound
Chemical reduction
Stereoselectivity
Ester
Chirality
Organic fluorine compounds
Formate
Platinoid Complexes
Monodentate ligand
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The regioselective palladium-catalyzed formate reduction of γ-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the γ position, the corresponding reduction products with a fluoroalkyl group at the tertiary carbon being afforded in high yields. When the chiral allylic ester was employed, complete chirality transfer was observed, leading to the optically active materials in high yields.
Bibliography:ark:/67375/TPS-DN8H3ZL6-8
istex:634E4B9201E78C2FC90383A5E12A628668525FB8
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0602120