An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate

Sven P. Fritz; Juan F. Moya; Matthew G. Unthank; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1055/s-0031-1290951

An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate

Sven P. Fritz, Juan F. Moya, Matthew G. Unthank, Eoghan M. McGarrigle^*, Varinder K. Aggarwal

^*Corresponding author for this work

School of Chemistry

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

36 Citations (Scopus)

Abstract

Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesis of an oxetane.

Original language	English
Pages (from-to)	1584-1590
Number of pages	7
Journal	Synthesis (Germany)
Volume	44
Issue number	10
DOIs	https://doi.org/10.1055/s-0031-1290951
Publication status	Published - May 2012

Keywords

annulations
cyclizations
heterocycles
sulfur
ylides
VINYL SULFONIUM SALTS
ASYMMETRIC-SYNTHESIS
DRUG DISCOVERY
AZETIDINE-2-CARBOXYLIC ACID
CYCLOPROPANATION REACTIONS
CONVENIENT METHOD
CHIRAL CATALYSTS
TANDEM REACTIONS
AMINO-ALCOHOLS
DERIVATIVES

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10.1055/s-0031-1290951

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

Cite this

@article{ceb32ef6f31d47b3bf827e38189b9b1f,

title = "An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate",

abstract = "Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesis of an oxetane.",

keywords = "annulations, cyclizations, heterocycles, sulfur, ylides, VINYL SULFONIUM SALTS, ASYMMETRIC-SYNTHESIS, DRUG DISCOVERY, AZETIDINE-2-CARBOXYLIC ACID, CYCLOPROPANATION REACTIONS, CONVENIENT METHOD, CHIRAL CATALYSTS, TANDEM REACTIONS, AMINO-ALCOHOLS, DERIVATIVES",

author = "Fritz, {Sven P.} and Moya, {Juan F.} and Unthank, {Matthew G.} and McGarrigle, {Eoghan M.} and Aggarwal, {Varinder K.}",

year = "2012",

month = may,

doi = "10.1055/s-0031-1290951",

language = "English",

volume = "44",

pages = "1584--1590",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

}

TY - JOUR

T1 - An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate

AU - Fritz, Sven P.

AU - Moya, Juan F.

AU - Unthank, Matthew G.

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2012/5

Y1 - 2012/5

N2 - Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesis of an oxetane.

AB - Easily accessible arylglycine derivatives were cyclized to azetidines by using commercially available (2-bromoethyl)sulfonium triflate in a simple and mild procedure. The high-yielding reaction has a relatively broad scope and was extended to the synthesis of an oxetane.

KW - annulations

KW - cyclizations

KW - heterocycles

KW - sulfur

KW - ylides

KW - VINYL SULFONIUM SALTS

KW - ASYMMETRIC-SYNTHESIS

KW - DRUG DISCOVERY

KW - AZETIDINE-2-CARBOXYLIC ACID

KW - CYCLOPROPANATION REACTIONS

KW - CONVENIENT METHOD

KW - CHIRAL CATALYSTS

KW - TANDEM REACTIONS

KW - AMINO-ALCOHOLS

KW - DERIVATIVES

U2 - 10.1055/s-0031-1290951

DO - 10.1055/s-0031-1290951

M3 - Article (Academic Journal)

SN - 0039-7881

VL - 44

SP - 1584

EP - 1590

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 10

ER -

An Efficient Synthesis of Azetidines with (2-Bromoethyl)sulfonium Triflate

Abstract

Keywords

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Projects

GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS

NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

Cite this