Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

Zheng Xue; Veronica M. Dee; Louisa J. Hope-Weeks; Bruce R. Whittlesey; Michael F. Mayer

doi:10.3998/ark.5550190.0011.706

Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

Zheng Xue, Veronica M. Dee, Louisa J. Hope-Weeks, Bruce R. Whittlesey, Michael F. Mayer

Chemistry and Biochemistry

Research output: Contribution to journal › Article

4 Scopus citations

Abstract

Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.

Original language	English
Pages (from-to)	65-80
Number of pages	16
Journal	Unknown Journal
Volume	2010
Issue number	7
DOIs	https://doi.org/10.3998/ark.5550190.0011.706
State	Published - 2010

Keywords

Aziridines
N-sulfinyl imines
Phenyldiazomethane
Sulfur ylides

Access to Document

10.3998/ark.5550190.0011.706

Link to publication in Scopus

Fingerprint Dive into the research topics of 'Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides'. Together they form a unique fingerprint.

Cite this

@article{c496723cabf64ad993e3cc6c6e3bdbc8,

title = "Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides",

abstract = "Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.",

keywords = "Aziridines, N-sulfinyl imines, Phenyldiazomethane, Sulfur ylides",

author = "Zheng Xue and Dee, {Veronica M.} and Hope-Weeks, {Louisa J.} and Whittlesey, {Bruce R.} and Mayer, {Michael F.}",

year = "2010",

doi = "10.3998/ark.5550190.0011.706",

language = "English",

volume = "2010",

pages = "65--80",

journal = "Unknown Journal",

number = "7",

}

TY - JOUR

T1 - Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

AU - Xue, Zheng

AU - Dee, Veronica M.

AU - Hope-Weeks, Louisa J.

AU - Whittlesey, Bruce R.

AU - Mayer, Michael F.

PY - 2010

Y1 - 2010

N2 - Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.

AB - Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.

KW - Aziridines

KW - N-sulfinyl imines

KW - Phenyldiazomethane

KW - Sulfur ylides

UR - http://www.scopus.com/inward/record.url?scp=77953455581&partnerID=8YFLogxK

U2 - 10.3998/ark.5550190.0011.706

DO - 10.3998/ark.5550190.0011.706

M3 - Article

AN - SCOPUS:77953455581

VL - 2010

SP - 65

EP - 80

JO - Unknown Journal

JF - Unknown Journal

IS - 7

ER -