Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues

Jonathan Clayden; Sean Parris; Nuria Cabedo; Andrew H. Payne

doi:10.1002/anie.200801078

Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues

Jonathan Clayden^*, Sean Parris, Nuria Cabedo, Andrew H. Payne

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

31 Citations (Scopus)

Abstract

(Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.

Original language	English
Pages (from-to)	5060-5062
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	27
Early online date	2 Jun 2008
DOIs	https://doi.org/10.1002/anie.200801078
Publication status	Published - 23 Jun 2008

Research Groups and Themes

Organic & Biological

Keywords

Carbohydrates
Dearomatization
Diastereoselectivity
Oxazolines
Pseudosugars

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title = "Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues",

abstract = "(Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.",

keywords = "Carbohydrates, Dearomatization, Diastereoselectivity, Oxazolines, Pseudosugars",

author = "Jonathan Clayden and Sean Parris and Nuria Cabedo and Payne, \{Andrew H.\}",

year = "2008",

month = jun,

day = "23",

doi = "10.1002/anie.200801078",

language = "English",

volume = "47",

pages = "5060--5062",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons, Ltd.",

number = "27",

}

TY - JOUR

T1 - Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings

T2 - A route to carbocyclic sugar analogues

AU - Clayden, Jonathan

AU - Parris, Sean

AU - Cabedo, Nuria

AU - Payne, Andrew H.

PY - 2008/6/23

Y1 - 2008/6/23

N2 - (Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.

AB - (Chemical Equation Presented) Versatile synthetic intermediates were formed by the dearomatization of 2-aryl 4,5-diphenyloxazolines with secondary alkyl lithium reagents in the presence of N,N′-dimethylpropyleneurea (DMPU; see scheme). The resulting cyclohexadiene derivatives were converted into carbocyclic analogues of mannose and altrose in a short sequence without the use of protecting groups.

KW - Carbohydrates

KW - Dearomatization

KW - Diastereoselectivity

KW - Oxazolines

KW - Pseudosugars

UR - https://www.scopus.com/pages/publications/49849100686

U2 - 10.1002/anie.200801078

DO - 10.1002/anie.200801078

M3 - Article (Academic Journal)

C2 - 18512216

AN - SCOPUS:49849100686

SN - 1433-7851

VL - 47

SP - 5060

EP - 5062

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 27

ER -

Stereoselective dearomatizing addition of nucleophiles to uncomplexed benzene rings: A route to carbocyclic sugar analogues

Abstract

Research Groups and Themes

Keywords

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