Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes

被引：50

作者：

Ahmad, Simon M.

Braddock, D. Christopher ^{[1
]}

Cansell, Gemma

Hermitage, Stephen A.

Redmond, Joanna M.

White, Andrew J. P.

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 34期

基金：

英国工程与自然科学研究理事会;

关键词：

Alkenes; Amidine; Electrophilic bromination; Organocatalysis;

D O I：

10.1016/j.tetlet.2007.06.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+/-)-iso-Amarine is a potent organocatalyst at 1 mol% loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple bromoamidine with an N-Br bond has been characterised crystallographically for the first time. Asymmetric induction in the bromination reactions with enantiopure amidines was zero. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5948 / 5952

页数：5

共 21 条

[1] Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
Ahmad, Simon M.
Braddock, D. Christopher
Cansell, Gemma
Hermitage, Stephen A.
[J]. TETRAHEDRON LETTERS, 2007, 48 (06) : 915 - 918
[2] Armstrong SK, 1999, SYNTHESIS-STUTTGART, P993
[3] Fractional crystallisation of (±)-iso-amarine with mandelic acid:: convenient access to (R,R)- and (S,S)-1,2-diamino-1,2-diphenylethanes
Braddock, D. Christopher
Hermitage, Stephen A.
Redmond, Joanna M.
White, Andrew J. P.
[J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2935 - 2937
[4] Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes
Braddock, D. Christopher
Cansell, Gemma
Hermitage, Stephen A.
[J]. CHEMICAL COMMUNICATIONS, 2006, (23) : 2483 - 2485
[5] A convenient preparation of enantiomerically pure (+)-(1R,2R)-and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes
Braddock, D. Christopher
Redmond, Joanna M.
Hermitage, Stephen A.
White, Andrew J. P.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) : 911 - 916
[6] DELAMARE PBD, 1982, ELECTROPHILIC ADDITI, P136
[7] New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis
El-Qisairi, AK
Qaseer, HA
Katsigras, G
Lorenzi, P
Trivedi, U
Tracz, S
Hartman, A
Miller, JA
Henry, PM
[J]. ORGANIC LETTERS, 2003, 5 (04) : 439 - 441
[8] ABSOLUTE CONFIGURATION AND CIRCULAR DICHROISM OF OPTICALLY ACTIVE (2.2)PARACYCLOPHANE DERIVATIVES
FALK, H
REICHROH.P
SCHLOGL, K
[J]. TETRAHEDRON, 1970, 26 (02) : 511 - &
[9] UBER N-HALOGENAMIDINE .2. DER AUSTAUSCH DES HALOGENS GEGEN DIE CYAN-GRUPPE
GOERDELER, J
LOEVENICH, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1953, 86 (07): : 890 - 894
[10] SYNTHESIS, SPECTROSCOPY, AND STRUCTURES OF 2-BROMO-1-BROMOIMINO-3-OXO-ISOINDOLINE(III) AND 1-BROMOIMINO-3-OXOISOINDOLINE(IV)
GREENWOOD, PA
LADD, MFC
POVEY, DC
[J]. JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1992, 22 (03): : 259 - 263

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