β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

Alexander J. Cresswell; Stephen G. Davies; James A. Lee; Paul M. Roberts; Angela J. Russell; James E. Thomson; Melloney J. Tyte

doi:10.1021/ol100862s

β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

Alexander J. Cresswell, Stephen G. Davies, James A. Lee, Paul M. Roberts, Angela J. Russell, James E. Thomson, Melloney J. Tyte

Research output: Contribution to journal › Article › peer-review

59 Citations (SciVal)

Abstract

A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF₃-OEt ₂ in CH₂Cl₂ at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S_N1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.

Original language	English
Pages (from-to)	2936-2939
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	13
DOIs	https://doi.org/10.1021/ol100862s
Publication status	Published - 2 Jul 2010

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

Access to Document

10.1021/ol100862s

Cite this

@article{524692aff02243188ab1c6e56e6a9105,

title = "β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides",

abstract = "A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.",

author = "Cresswell, \{Alexander J.\} and Davies, \{Stephen G.\} and Lee, \{James A.\} and Roberts, \{Paul M.\} and Russell, \{Angela J.\} and Thomson, \{James E.\} and Tyte, \{Melloney J.\}",

year = "2010",

month = jul,

day = "2",

doi = "10.1021/ol100862s",

language = "English",

volume = "12",

pages = "2936--2939",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

AU - Cresswell, Alexander J.

AU - Davies, Stephen G.

AU - Lee, James A.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Thomson, James E.

AU - Tyte, Melloney J.

PY - 2010/7/2

Y1 - 2010/7/2

N2 - A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.

AB - A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.

UR - http://www.scopus.com/inward/record.url?scp=77954103643&partnerID=8YFLogxK

UR - https://doi.org/10.1021/ol100862s

U2 - 10.1021/ol100862s

DO - 10.1021/ol100862s

M3 - Article

C2 - 20509635

AN - SCOPUS:77954103643

SN - 1523-7060

VL - 12

SP - 2936

EP - 2939

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

β-Fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this