Asymmetric aziridination of chalcone promoted by binaphthalene-based chiral amines

Philip Bulman Page; Celine Bordogna; Ian Strutt; Yohan Chan; Benjamin R. Buckley

doi:10.1055/s-0033-1339643

Asymmetric aziridination of chalcone promoted by binaphthalene-based chiral amines

Philip Bulman Page, Celine Bordogna, Ian Strutt, Yohan Chan, Benjamin R. Buckley

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

14 Citations (Scopus)

Abstract

Aminimines derived in situ from a number of enantiomerically pure binaphthalene-based tertiary amines have been used for the asymmetric aziridination of chalcone, providing N-unprotected aziridines with ee values of up to 43%. A chiral hydrazinium salt has been isolated for the first time and shown to provide similar yield and enantioselectivity to the in situ process in reaction with chalcone.

Original language	English
Pages (from-to)	2067-2072
Number of pages	6
Journal	Synlett
Volume	24
Issue number	16
DOIs	https://doi.org/10.1055/s-0033-1339643
Publication status	Published - 1 Oct 2013

Keywords

chalcone
aziridination
binaphthalene-based tertiary amines

Access to Document

10.1055/s-0033-1339643

Cite this

@article{34375069bc5c46f39fae657e1e4d66fb,

title = "Asymmetric aziridination of chalcone promoted by binaphthalene-based chiral amines",

abstract = "Aminimines derived in situ from a number of enantiomerically pure binaphthalene-based tertiary amines have been used for the asymmetric aziridination of chalcone, providing N-unprotected aziridines with ee values of up to 43%. A chiral hydrazinium salt has been isolated for the first time and shown to provide similar yield and enantioselectivity to the in situ process in reaction with chalcone.",

keywords = "chalcone, aziridination, binaphthalene-based tertiary amines",

author = "{Bulman Page}, Philip and Celine Bordogna and Ian Strutt and Yohan Chan and Buckley, {Benjamin R.}",

year = "2013",

month = oct,

day = "1",

doi = "10.1055/s-0033-1339643",

language = "English",

volume = "24",

pages = "2067--2072",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "16",

}

TY - JOUR

T1 - Asymmetric aziridination of chalcone promoted by binaphthalene-based chiral amines

AU - Bulman Page, Philip

AU - Bordogna, Celine

AU - Strutt, Ian

AU - Chan, Yohan

AU - Buckley, Benjamin R.

PY - 2013/10/1

Y1 - 2013/10/1

N2 - Aminimines derived in situ from a number of enantiomerically pure binaphthalene-based tertiary amines have been used for the asymmetric aziridination of chalcone, providing N-unprotected aziridines with ee values of up to 43%. A chiral hydrazinium salt has been isolated for the first time and shown to provide similar yield and enantioselectivity to the in situ process in reaction with chalcone.

AB - Aminimines derived in situ from a number of enantiomerically pure binaphthalene-based tertiary amines have been used for the asymmetric aziridination of chalcone, providing N-unprotected aziridines with ee values of up to 43%. A chiral hydrazinium salt has been isolated for the first time and shown to provide similar yield and enantioselectivity to the in situ process in reaction with chalcone.

KW - chalcone

KW - aziridination

KW - binaphthalene-based tertiary amines

U2 - 10.1055/s-0033-1339643

DO - 10.1055/s-0033-1339643

M3 - Article

SN - 0936-5214

VL - 24

SP - 2067

EP - 2072

JO - Synlett

JF - Synlett

IS - 16

ER -