Stereochemical studies of chiral acyclic nitroxides coupling with a prochiral radical

Rebecca Braslau; Vladimir Chaplinski; Aaron Nilsen; Navamoney Arulsamy

doi:10.1081/SCC-120039497

Stereochemical studies of chiral acyclic nitroxides coupling with a prochiral radical

Rebecca Braslau, Vladimir Chaplinski, Aaron Nilsen, Navamoney Arulsamy

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

2 Scopus citations

Abstract

A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1-phenethyl. In one case, an x-ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.

Original language	English (US)
Pages (from-to)	2433-2442
Number of pages	10
Journal	Synthetic Communications
Volume	34
Issue number	13
DOIs	https://doi.org/10.1081/SCC-120039497
State	Published - 2004
Externally published	Yes

Keywords

Diastereoselectivity
N-Alkoxyamine
Nitroxide
Prochiral radical

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1081/SCC-120039497

Cite this

@article{0bbb24f9d76e4a87857209e8d31cb709,

title = "Stereochemical studies of chiral acyclic nitroxides coupling with a prochiral radical",

abstract = "A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1-phenethyl. In one case, an x-ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.",

keywords = "Diastereoselectivity, N-Alkoxyamine, Nitroxide, Prochiral radical",

author = "Rebecca Braslau and Vladimir Chaplinski and Aaron Nilsen and Navamoney Arulsamy",

note = "Funding Information: Financial support from the National Science Foundation (CHE 9527647 and CHE 0078852) is gratefully acknowledged.",

year = "2004",

doi = "10.1081/SCC-120039497",

language = "English (US)",

volume = "34",

pages = "2433--2442",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "13",

}

TY - JOUR

T1 - Stereochemical studies of chiral acyclic nitroxides coupling with a prochiral radical

AU - Braslau, Rebecca

AU - Chaplinski, Vladimir

AU - Nilsen, Aaron

AU - Arulsamy, Navamoney

N1 - Funding Information: Financial support from the National Science Foundation (CHE 9527647 and CHE 0078852) is gratefully acknowledged.

PY - 2004

Y1 - 2004

N2 - A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1-phenethyl. In one case, an x-ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.

AB - A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1-phenethyl. In one case, an x-ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.

KW - Diastereoselectivity

KW - N-Alkoxyamine

KW - Nitroxide

KW - Prochiral radical

UR - http://www.scopus.com/inward/record.url?scp=3543050711&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=3543050711&partnerID=8YFLogxK

U2 - 10.1081/SCC-120039497

DO - 10.1081/SCC-120039497

M3 - Article

AN - SCOPUS:3543050711

SN - 0039-7911

VL - 34

SP - 2433

EP - 2442

JO - Synthetic Communications

JF - Synthetic Communications

IS - 13

ER -

Stereochemical studies of chiral acyclic nitroxides coupling with a prochiral radical

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this