(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

Sven P. Fritz; Zulfiquar Ali; Matthew G. Unthank; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1002/hlca.201200455

(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

Sven P. Fritz, Zulfiquar Ali, 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

16 Citations (Scopus)

Abstract

A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridine?fused heterocycles (up to 98% yield, up to 96?:?4 er or up to 15?:?1 dr), using a tandem Michael addition/Johnson?Corey?Chaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

Original language	English
Pages (from-to)	2384-2398
Number of pages	15
Journal	Helvetica Chimica Acta
Volume	95
Issue number	12
DOIs	https://doi.org/10.1002/hlca.201200455
Publication status	Published - Dec 2012

Keywords

Ylides
Johnson?Corey?Chaykovsky annulations
Cyclization reactions
Sulfides
Stereoselective synthesis
VINYL SULFONIUM SALTS
CONVENIENT METHOD
ENANTIOSELECTIVE SYNTHESIS
ASYMMETRIC EPOXIDATION
ALPHA-IMIDOSTYRENES
EFFICIENT SYNTHESIS
TANDEM REACTIONS
AMINO-ALCOHOLS
AMPHOTERICIN-B
DERIVATIVES

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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{47b1730cc9bb438ab3ee5321333c28e9,

title = "(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines",

abstract = "A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridine?fused heterocycles (up to 98% yield, up to 96?:?4 er or up to 15?:?1 dr), using a tandem Michael addition/Johnson?Corey?Chaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.",

keywords = "Ylides, Johnson?Corey?Chaykovsky annulations, Cyclization reactions, Sulfides, Stereoselective synthesis, VINYL SULFONIUM SALTS, CONVENIENT METHOD, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC EPOXIDATION, ALPHA-IMIDOSTYRENES, EFFICIENT SYNTHESIS, TANDEM REACTIONS, AMINO-ALCOHOLS, AMPHOTERICIN-B, DERIVATIVES",

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

year = "2012",

month = dec,

doi = "10.1002/hlca.201200455",

language = "English",

volume = "95",

pages = "2384--2398",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Wiley",

number = "12",

}

TY - JOUR

T1 - (2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

AU - Fritz, Sven P.

AU - Ali, Zulfiquar

AU - Unthank, Matthew G.

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2012/12

Y1 - 2012/12

N2 - A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridine?fused heterocycles (up to 98% yield, up to 96?:?4 er or up to 15?:?1 dr), using a tandem Michael addition/Johnson?Corey?Chaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

AB - A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridine?fused heterocycles (up to 98% yield, up to 96?:?4 er or up to 15?:?1 dr), using a tandem Michael addition/Johnson?Corey?Chaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

KW - Ylides

KW - Johnson?Corey?Chaykovsky annulations

KW - Cyclization reactions

KW - Sulfides

KW - Stereoselective synthesis

KW - VINYL SULFONIUM SALTS

KW - CONVENIENT METHOD

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ASYMMETRIC EPOXIDATION

KW - ALPHA-IMIDOSTYRENES

KW - EFFICIENT SYNTHESIS

KW - TANDEM REACTIONS

KW - AMINO-ALCOHOLS

KW - AMPHOTERICIN-B

KW - DERIVATIVES

U2 - 10.1002/hlca.201200455

DO - 10.1002/hlca.201200455

M3 - Article (Academic Journal)

SN - 0018-019X

VL - 95

SP - 2384

EP - 2398

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 12

ER -

(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

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