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Christopher D. Bray

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Organization: Queen Mary University of London , England
Department: School of Biological and Chemical Sciences
Title: Lecture(PhD)

TOPICS

Spiroketal Formation by Cascade Oxidative Dearomatization: An Approach to the Phorbaketal Skeleton
Co-reporter:Harry J. Shirley
European Journal of Organic Chemistry 2016 Volume 2016( Issue 8) pp:1504-1507
Publication Date(Web):
DOI:10.1002/ejoc.201501370

Abstract

Addition of PhI(OAc)2 to phenols that have meta-linked hydroxy ketones results in cascade oxidative dearomatizing spirocyclization to give tricyclic spiroketals. This framework is found in the phorbaketal family of natural products.

An ortho-quinone methide based strategy towards the rubromycin spiroketal family
Co-reporter:N. J. Willis and C. D. Bray  
RSC Advances 2015 vol. 5(Issue 98) pp:80212-80215
Publication Date(Web):10 Sep 2015
DOI:10.1039/C5RA17108C
A method for the generation/in situ hetero-Diels–Alder cycloaddition of a trisubstituted ortho-quinone methide (o-QM) is described. Heating of ortho-hydroxybenzylamines was found to be a more effective strategy for the formation of o-QMs than use of the corresponding N-substituted quaternary salts hitherto employed. This method was used to synthesise the spiroketal core of the rubromycins.
Sultones and Sultines via a JuliaKocienski Reaction of Epoxides
Co-reporter:Dr. Geoffrey M. T. Smith;Dr. Paul M. Burton;Dr. Christopher D. Bray
Angewandte Chemie International Edition 2015 Volume 54( Issue 50) pp:15236-15240
Publication Date(Web):
DOI:10.1002/anie.201508467

Abstract

The development of the homologous Julia–Kocienski reaction has led to the discovery of two new reaction modes of epoxides with sulfones. These pathways allow rapid and direct access to a range of γ-sultones and γ-sultines.

Sultones and Sultines via a JuliaKocienski Reaction of Epoxides
Co-reporter:Dr. Geoffrey M. T. Smith;Dr. Paul M. Burton;Dr. Christopher D. Bray
Angewandte Chemie 2015 Volume 127( Issue 50) pp:15451-15455
Publication Date(Web):
DOI:10.1002/ange.201508467

Abstract

The development of the homologous Julia–Kocienski reaction has led to the discovery of two new reaction modes of epoxides with sulfones. These pathways allow rapid and direct access to a range of γ-sultones and γ-sultines.

Direct conversion of epoxides into aziridines with N-arylphosphoramidates
Co-reporter:Fabrizio Minicone, Wendy J. Rogers, James F.J. Green, Mommna Khan, Geoffrey M.T. Smith, Christopher D. Bray
Tetrahedron Letters 2014 Volume 55(Issue 43) pp:5890-5891
Publication Date(Web):22 October 2014
DOI:10.1016/j.tetlet.2014.08.009
Treatment of terminal epoxides with N-arylphosphoramidate anions leads directly to N-aryl aziridines. Existing methods for this transformation employ either multi-step syntheses or an iminophosphorane in conjunction with a Lewis acid. The described method therefore presents an advantage in terms of brevity and atom economy.
ortho-Quinone Methides in Natural Product Synthesis
Co-reporter:Nicky J. Willis ;Dr. Christopher D. Bray
Chemistry - A European Journal 2012 Volume 18( Issue 30) pp:9160-9173
Publication Date(Web):
DOI:10.1002/chem.201200619

Abstract

ortho-Quinone methides (o-QMs) are emerging as highly useful intermediates, the inherent reactivity of which can be used in linchpin reactions for the construction of complex natural products. This review encompasses the major contributions in this field, exemplifying the major strategies and reactivity modes which can be applied.

Stereocontrolled synthesis of quaternary cyclopropyl esters
Co-reporter:Christopher D. Bray and Fabrizio Minicone  
Chemical Communications 2010 vol. 46(Issue 32) pp:5867-5869
Publication Date(Web):13 Jul 2010
DOI:10.1039/C0CC01333A
Treatment of a variety of enantiopure terminal epoxides with the anion of a range of 2-substituted triethylphosphonoacetates leads to an array of quaternary cyclopropyl esters with high yield and diastereocontrol.
Stereocontrolled Synthesis of trans-Cyclopropyl Sulfones from Terminal Epoxides
Co-reporter:Christopher D. Bray and Giorgio de Faveri
The Journal of Organic Chemistry 2010 Volume 75(Issue 13) pp:4652-4655
Publication Date(Web):June 10, 2010
DOI:10.1021/jo100844g
Treatment of a range of (enantiopure) epoxides with the sodium salt of diethyl (phenylsulfonyl)methylphosphonate in DME at 140 °C for 4 h gives a variety of (enantiopure) trans-cyclopropyl sulfones with high diastereoselectivity.
Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals
Co-reporter:Christopher D. Bray  
Organic & Biomolecular Chemistry 2008 vol. 6(Issue 15) pp:2815-2819
Publication Date(Web):28 May 2008
DOI:10.1039/B806593D
Deprotonation of o-hydroxybenzyl acetate with iPrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2π partners in hetero-Diels–Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.
Generation and hetero-Diels–Alder reactions of an o-quinone methide under mild, anionic conditions: rapid synthesis of mono-benzannelated spiroketals
Co-reporter:Christopher D. Bray
Organic & Biomolecular Chemistry 2008 - vol. 6(Issue 15) pp:NaN2819-2819
Publication Date(Web):2008/05/28
DOI:10.1039/B806593D
Deprotonation of o-hydroxybenzyl acetate with iPrMgCl provides a method of generating an o-quinone methide under mild, anionic conditions, such that highly sensitive exo-enol ethers can be employed as 2π partners in hetero-Diels–Alder reactions. This process results in mono-benzannelated spiroketals such as those found in the natural products berkelic acid, the chaetoquadrins or cephalostatin 6.
Stereocontrolled synthesis of quaternary cyclopropyl esters
Co-reporter:Christopher D. Bray and Fabrizio Minicone
Chemical Communications 2010 - vol. 46(Issue 32) pp:NaN5869-5869
Publication Date(Web):2010/07/13
DOI:10.1039/C0CC01333A
Treatment of a variety of enantiopure terminal epoxides with the anion of a range of 2-substituted triethylphosphonoacetates leads to an array of quaternary cyclopropyl esters with high yield and diastereocontrol.
1,2-Oxathiolane, 3,3,5-trimethyl-, 2-oxide, (2R,5R)-rel-
1,2-Oxathiolane, 3,3,5-trimethyl-, 2-oxide, (2R,5R)-rel-
CAS:512178-68-6
1,2-Oxathiolane, 3,3,5-trimethyl-, 2-oxide, (2R,5R)-rel-
Propanamide, 2-(acetyloxy)-, (S)-
Propanamide, 2-(acetyloxy)-, (S)-
CAS:50911-24-5
Propanamide, 2-(acetyloxy)-, (S)-
2H,5H-Pyrano[2,3-b][1]benzopyran, 3,4,4a,10a-tetrahydro-, cis-
2H,5H-Pyrano[2,3-b][1]benzopyran, 3,4,4a,10a-tetrahydro-, cis-
CAS:33649-22-8
2H,5H-Pyrano[2,3-b][1]benzopyran, 3,4,4a,10a-tetrahydro-, cis-
CYCLOPROPANECARBOXYLIC ACID, 1-METHYL-2-PHENYL-, ETHYL ESTER, (1R,2S)-
CYCLOPROPANECARBOXYLIC ACID, 1-METHYL-2-PHENYL-, ETHYL ESTER, (1R,2S)-
CAS:536745-42-3
CYCLOPROPANECARBOXYLIC ACID, 1-METHYL-2-PHENYL-, ETHYL ESTER, (1R,2S)-
OXIRANE, (4-PHENYLBUTYL)-
OXIRANE, (4-PHENYLBUTYL)-
CAS:86088-39-3
OXIRANE, (4-PHENYLBUTYL)-
2H-Pyran, tetrahydro-2-methylene-
2H-Pyran, tetrahydro-2-methylene-
CAS:38614-15-2
2H-Pyran, tetrahydro-2-methylene-
(2S)-2-benzyloxirane
(2S)-2-benzyloxirane
CAS:61393-94-0
(2S)-2-benzyloxirane
2-(acetoxymethyl)phenol
2-(acetoxymethyl)phenol
CAS:6161-96-2
2-(acetoxymethyl)phenol
2-Methylenetetrahydrofuran
2-Methylenetetrahydrofuran
CAS:18137-88-7
2-Methylenetetrahydrofuran
Silane, (1,1-dimethylethyl)(4-methoxyphenoxy)dimethyl-
Silane, (1,1-dimethylethyl)(4-methoxyphenoxy)dimethyl-
CAS:62790-87-8
Silane, (1,1-dimethylethyl)(4-methoxyphenoxy)dimethyl-