A stereocontrolled access to vicinal difluoroalkanes
1988
Abstract
An expedient method for the prepn. of diastereomerically and, by extension, even enantiomerically pure vicinal difluoroalkanes is described. The two fluorine atoms are introduced in two consecutive steps: ring opening of an oxirane by addn. of hydrogen fluoride and subsequent treatment of the resulting hydroxy fluoride with diethylaminosulfur trifluorides. Thus, sep. treatment of (E)- and (Z)-RCH:CHR [R = (CH2)4Me] via epoxidn., HF addn, and fluorination, gave dl- or meso-RCHFCHFR, resp. [on SciFinder (R)]
Details
Title
A stereocontrolled access to vicinal difluoroalkanes
Author(s)
Hamatani, Takeshi ; Matsubara, Seijiro ; Matsuda, Hiroyuki ; Schlosser, Manfred
Published in
Tetrahedron
Volume
44
Issue
10
Pages
2875-2881
Date
1988
ISSN
0040-4020
Keywords
Asymmetric synthesis and induction (of vicinal difluoroalkanes); Fluorination (stereoselective; of alkenes via epoxidn.; fluoride ring opening; and reaction with diethylaminosulfur trifluoride; vicinal difluoroalkanes from); alkene stereoselective vicinal fluorination; epoxide stereoselective vicinal fluorination; difluoroalkane vicinal stereoselective prepn
Note
CAN 110:94451
23-3
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
130888-52-7 Role: RCT (Reactant), RACT (Reactant or reagent) (fluorination of, with diethylaminosulfur trifluoride); 7782-41-4 Role: RCT (Reactant), RACT (Reactant or reagent) (fluorination, stereoselective, of alkenes via epoxidn., fluoride ring opening, and reaction with diethylaminosulfur trifluoride, vicinal difluoroalkanes from); 7206-17-9P (trans-6-Dodecene); 7206-29-3P (cis-6-Dodecene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and epoxidn. of, with monoperphthalic acid); 130876-18-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and fluorination of); 92943-15-2P (cis-6,7-Epoxydodecane); 92943-16-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ring opening of, with hydrogen fluoride-triethylamine complex); 119105-44-1P; 119105-45-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 4762-26-9 (Hexyl triphenylphosphonium bromide) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective Wittig reaction of, with hexanal); 66-25-1 (Hexanal) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective Wittig reaction of, with hexyltriphenylphosphonium bromide)
23-3
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
130888-52-7 Role: RCT (Reactant), RACT (Reactant or reagent) (fluorination of, with diethylaminosulfur trifluoride); 7782-41-4 Role: RCT (Reactant), RACT (Reactant or reagent) (fluorination, stereoselective, of alkenes via epoxidn., fluoride ring opening, and reaction with diethylaminosulfur trifluoride, vicinal difluoroalkanes from); 7206-17-9P (trans-6-Dodecene); 7206-29-3P (cis-6-Dodecene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and epoxidn. of, with monoperphthalic acid); 130876-18-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and fluorination of); 92943-15-2P (cis-6,7-Epoxydodecane); 92943-16-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ring opening of, with hydrogen fluoride-triethylamine complex); 119105-44-1P; 119105-45-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 4762-26-9 (Hexyl triphenylphosphonium bromide) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective Wittig reaction of, with hexanal); 66-25-1 (Hexanal) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective Wittig reaction of, with hexyltriphenylphosphonium bromide)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03