Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts

Sven P. Fritz; Thomas H. West; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1021/ol303200n

Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts

Sven P. Fritz, Thomas H. West, Eoghan M. McGarrigle^*, Varinder K. Aggarwal

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

53 Citations (Scopus)

Abstract

CF3-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of alpha-CF3 substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr>20:1).

Original language	English
Pages (from-to)	6370-6373
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	24
DOIs	https://doi.org/10.1021/ol303200n
Publication status	Published - 21 Dec 2012

Research Groups and Themes

Organic & Biological

Keywords

VINYL SULFONIUM SALTS
MEDICINAL CHEMISTRY
CONVENIENT METHOD
STRAIGHTFORWARD SYNTHESIS
ASYMMETRIC-SYNTHESIS
ALPHA-IMIDOSTYRENES
EFFICIENT SYNTHESIS
TANDEM REACTIONS
FLUORINE
TRIFLATE

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10.1021/ol303200n

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GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/07 → 1/04/13
Project: Research
NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

Cite this

@article{33b11e91e5474220b80b9c871a6b4ed5,

title = "Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts",

abstract = "CF3-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of alpha-CF3 substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr>20:1).",

keywords = "VINYL SULFONIUM SALTS, MEDICINAL CHEMISTRY, CONVENIENT METHOD, STRAIGHTFORWARD SYNTHESIS, ASYMMETRIC-SYNTHESIS, ALPHA-IMIDOSTYRENES, EFFICIENT SYNTHESIS, TANDEM REACTIONS, FLUORINE, TRIFLATE",

author = "Fritz, \{Sven P.\} and West, \{Thomas H.\} and McGarrigle, \{Eoghan M.\} and Aggarwal, \{Varinder K.\}",

year = "2012",

month = dec,

day = "21",

doi = "10.1021/ol303200n",

language = "English",

volume = "14",

pages = "6370--6373",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts

AU - Fritz, Sven P.

AU - West, Thomas H.

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2012/12/21

Y1 - 2012/12/21

N2 - CF3-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of alpha-CF3 substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr>20:1).

AB - CF3-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of alpha-CF3 substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr>20:1).

KW - VINYL SULFONIUM SALTS

KW - MEDICINAL CHEMISTRY

KW - CONVENIENT METHOD

KW - STRAIGHTFORWARD SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - ALPHA-IMIDOSTYRENES

KW - EFFICIENT SYNTHESIS

KW - TANDEM REACTIONS

KW - FLUORINE

KW - TRIFLATE

U2 - 10.1021/ol303200n

DO - 10.1021/ol303200n

M3 - Article (Academic Journal)

C2 - 23231752

SN - 1523-7060

VL - 14

SP - 6370

EP - 6373

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts

Abstract

Research Groups and Themes

Keywords

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Projects

GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS

NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

Cite this