Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines

Philip C. Bulman Page; Benjamin R. Buckley; Mark R. J. Elsegood; Colin M. Hayman; Harry Heaney; Gerasimos A. Rassias; Salem A. Talib; John Liddle

doi:10.1016/j.tet.2007.08.053

Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines

Philip C. Bulman Page, Benjamin R. Buckley, Mark R. J. Elsegood, Colin M. Hayman, Harry Heaney, Gerasimos A. Rassias, Salem A. Talib, John Liddle

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

14 Citations (Scopus)

Abstract

A number of enantiomerically pure 1,2-aminoalcohols containing tertiary nitrogen atoms bearing chiral substituents have been prepared by highly diastereoselective reductive ring cleavage of oxazolidines derived from ketones and pseudoephedrine or ephedrine. The ring cleavage occurs with retention of configuration. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	10991-10999
Number of pages	9
Journal	Tetrahedron
Volume	63
Issue number	45
DOIs	https://doi.org/10.1016/j.tet.2007.08.053
Publication status	Published - 2007

Keywords

enantiomerically pure
aminoalcohol
KETONES
reductive cleavage
CLEAVAGE
AMINATION
oxazolidine
CONJUGATE ADDITION
HYDRIDE
stereoselective
PSEUDOEPHEDRINE
DERIVATIVES
OXAZOLINES
reduction
EPHEDRINE

Access to Document

10.1016/j.tet.2007.08.053

Cite this

@article{6ad9bf0d26bd493681aa76b8c3185d3d,

title = "Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines",

abstract = "A number of enantiomerically pure 1,2-aminoalcohols containing tertiary nitrogen atoms bearing chiral substituents have been prepared by highly diastereoselective reductive ring cleavage of oxazolidines derived from ketones and pseudoephedrine or ephedrine. The ring cleavage occurs with retention of configuration. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "enantiomerically pure, aminoalcohol, KETONES, reductive cleavage, CLEAVAGE, AMINATION, oxazolidine, CONJUGATE ADDITION, HYDRIDE, stereoselective, PSEUDOEPHEDRINE, DERIVATIVES, OXAZOLINES, reduction, EPHEDRINE",

author = "{Bulman Page}, {Philip C.} and Buckley, {Benjamin R.} and Elsegood, {Mark R. J.} and Hayman, {Colin M.} and Harry Heaney and Rassias, {Gerasimos A.} and Talib, {Salem A.} and John Liddle",

year = "2007",

doi = "10.1016/j.tet.2007.08.053",

language = "English",

volume = "63",

pages = "10991--10999",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "45",

}

TY - JOUR

T1 - Synthesis of enantiomerically pure tertiary 1,2-aminoalcohols by the highly diastereoselective reductive ring opening of oxazolidines

AU - Bulman Page, Philip C.

AU - Buckley, Benjamin R.

AU - Elsegood, Mark R. J.

AU - Hayman, Colin M.

AU - Heaney, Harry

AU - Rassias, Gerasimos A.

AU - Talib, Salem A.

AU - Liddle, John

PY - 2007

Y1 - 2007

N2 - A number of enantiomerically pure 1,2-aminoalcohols containing tertiary nitrogen atoms bearing chiral substituents have been prepared by highly diastereoselective reductive ring cleavage of oxazolidines derived from ketones and pseudoephedrine or ephedrine. The ring cleavage occurs with retention of configuration. (c) 2007 Elsevier Ltd. All rights reserved.

AB - A number of enantiomerically pure 1,2-aminoalcohols containing tertiary nitrogen atoms bearing chiral substituents have been prepared by highly diastereoselective reductive ring cleavage of oxazolidines derived from ketones and pseudoephedrine or ephedrine. The ring cleavage occurs with retention of configuration. (c) 2007 Elsevier Ltd. All rights reserved.

KW - enantiomerically pure

KW - aminoalcohol

KW - KETONES

KW - reductive cleavage

KW - CLEAVAGE

KW - AMINATION

KW - oxazolidine

KW - CONJUGATE ADDITION

KW - HYDRIDE

KW - stereoselective

KW - PSEUDOEPHEDRINE

KW - DERIVATIVES

KW - OXAZOLINES

KW - reduction

KW - EPHEDRINE

U2 - 10.1016/j.tet.2007.08.053

DO - 10.1016/j.tet.2007.08.053

M3 - Article

SN - 0040-4020

VL - 63

SP - 10991

EP - 10999

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -