The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol

Matthew G. Unthank; Nigel Hussain; Varinder K. Aggarwal

doi:10.1002/anie.200602782

The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol

Matthew G. Unthank^*, Nigel Hussain, Varinder K. Aggarwal

^*Corresponding author for this work

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

143 Citations (Scopus)

Abstract

(Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).

Original language	English
Pages (from-to)	7066-7069
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	42
DOIs	https://doi.org/10.1002/anie.200602782
Publication status	Published - 27 Oct 2006
Externally published	Yes

Keywords

Annulation
Asymmetric synthesis
Natural products
Ring opening
Sulfur ylides

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10.1002/anie.200602782

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title = "The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol",

abstract = "(Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).",

keywords = "Annulation, Asymmetric synthesis, Natural products, Ring opening, Sulfur ylides",

author = "Unthank, \{Matthew G.\} and Nigel Hussain and Aggarwal, \{Varinder K.\}",

year = "2006",

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day = "27",

doi = "10.1002/anie.200602782",

language = "English",

volume = "45",

pages = "7066--7069",

journal = "Angewandte Chemie - International Edition",

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The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol. / Unthank, Matthew G.; Hussain, Nigel; Aggarwal, Varinder K.
In: Angewandte Chemie - International Edition, Vol. 45, No. 42, 27.10.2006, p. 7066-7069.

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

TY - JOUR

T1 - The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles

T2 - Application to the synthesis of (-)-balanol

AU - Unthank, Matthew G.

AU - Hussain, Nigel

AU - Aggarwal, Varinder K.

PY - 2006/10/27

Y1 - 2006/10/27

N2 - (Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).

AB - (Chemical Equation Presented) Lift your ylides: An asymmetric, epoxy-annulation reaction mediated by a vinyl sulfonium salt converts aminoaldehydes and -ketones into fused heterocyclic epoxides. The methodology was extended to an aziridine-annulation reaction, which was used to complete the shortest known formal synthesis of balanol (see scheme, Ts = toluene-p-sulfonyl, Tf = trifluoromethanesulfonyl).

KW - Annulation

KW - Asymmetric synthesis

KW - Natural products

KW - Ring opening

KW - Sulfur ylides

UR - https://www.scopus.com/pages/publications/33750630993

U2 - 10.1002/anie.200602782

DO - 10.1002/anie.200602782

M3 - Article

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SN - 1433-7851

VL - 45

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EP - 7069

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 42

ER -

The use of vinyl sulfonium salts in the stereo-controlled asymmetric synthesis of epoxide- and aziridine-fused heterocycles: Application to the synthesis of (-)-balanol

Abstract

Keywords

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