Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Jonathan Clayden; Lai Wah Lai; Madeleine Helliwell

doi:10.1016/j.tet.2004.01.101

Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Jonathan Clayden, Lai Wah Lai, Madeleine Helliwell

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

Abstract

Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4399-4412
Number of pages	13
Journal	Tetrahedron
Volume	60
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2004.01.101
Publication status	Published - 10 May 2004

Keywords

Atropisomeric amides
Ephedrine
Imidazolines
Oxazolidines

Access to Document

10.1016/j.tet.2004.01.101

Cite this

@article{0246ce72925e4fd39a0e334555c5d9aa,

title = "Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines",

abstract = "Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. {\textcopyright} 2004 Elsevier Ltd. All rights reserved.",

keywords = "Atropisomeric amides, Ephedrine, Imidazolines, Oxazolidines",

author = "Jonathan Clayden and Lai, {Lai Wah} and Madeleine Helliwell",

year = "2004",

month = may,

day = "10",

doi = "10.1016/j.tet.2004.01.101",

language = "English",

volume = "60",

pages = "4399--4412",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier BV",

number = "20",

}

TY - JOUR

T1 - Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

AU - Clayden, Jonathan

AU - Lai, Lai Wah

AU - Helliwell, Madeleine

PY - 2004/5/10

Y1 - 2004/5/10

N2 - Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. © 2004 Elsevier Ltd. All rights reserved.

AB - Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. © 2004 Elsevier Ltd. All rights reserved.

KW - Atropisomeric amides

KW - Ephedrine

KW - Imidazolines

KW - Oxazolidines

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/cc7np5q&sid=DataCite

U2 - 10.1016/j.tet.2004.01.101

DO - 10.1016/j.tet.2004.01.101

M3 - Article

VL - 60

SP - 4399

EP - 4412

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 20

ER -

Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

CCDC 166016: Experimental Crystal Structure Determination

Cite this

Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 166016: Experimental Crystal Structure Determination

Cite this