(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

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

16 Citations (Scopus)

Abstract

A versatile and simple methodis reported for the synthesis of bicyclic epoxide and aziridineï£¿fused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ Johnsonï£¿Coreyï£¿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
Externally published	Yes

Keywords

Cyclization reactions
Johnsonï£¿Coreyï£¿Chaykovsky annulations
Stereoselective synthesis
Sulfides
Ylides

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10.1002/hlca.201200455

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

abstract = "A versatile and simple methodis reported for the synthesis of bicyclic epoxide and aziridine{\"i}£¿fused heterocycles (up to 98\% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ Johnson{\"i}£¿Corey{\"i}£¿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 = "Cyclization reactions, Johnson{\"i}£¿Corey{\"i}£¿Chaykovsky annulations, Stereoselective synthesis, Sulfides, Ylides",

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 = "Blackwell Publishing",

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 methodis reported for the synthesis of bicyclic epoxide and aziridineï£¿fused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ Johnsonï£¿Coreyï£¿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 methodis reported for the synthesis of bicyclic epoxide and aziridineï£¿fused heterocycles (up to 98% yield, up to 96: 4 er or up to 15: 1 dr), using a tandem Michael addition/ Johnsonï£¿Coreyï£¿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 - Cyclization reactions

KW - Johnsonï£¿Coreyï£¿Chaykovsky annulations

KW - Stereoselective synthesis

KW - Sulfides

KW - Ylides

UR - https://www.scopus.com/pages/publications/84872849521

U2 - 10.1002/hlca.201200455

DO - 10.1002/hlca.201200455

M3 - Article

AN - SCOPUS:84872849521

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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