Donald Westwood

University of Liverpool

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Philip C. Bulman Page

University of East Anglia

Monique B. van Niel

Charles River Laboratories (Netherlands)

Sukhbinder S. Klair

Loughborough University

Alexandra M. Z. Slawin

University of St Andrews

David J. Williams

Natural History Museum

Jeremy C. Prodger

GlaxoSmithKline (United Kingdom)

Jennifer Law

University of North Carolina at Chapel Hill

Rhiannon Harries

Swansea Bay University Health Board

Nilay Solanki

Charotar University of Science and Technology

Christine Bruce

University Health Network

Cooperative Institutions

University of Liverpool

Countess of Chester Hospital NHS Foundation Trust

University College London

University of Birmingham

Royal College of Surgeons of England

Royal College of Surgeons in Ireland

Association of Anaesthetists of Great Britain and Ireland

Guy's Hospital

Middlesex Hospital

University College Hospital

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Perkin communications. Diastereoselective alkylation of ketone enolates using a 1,3-dithiane 1-oxide auxiliary

Journal of the Chemical Society. Perkin transactions I/Journal of the Chemical Society. Perkin transactions. I (1989)

Philip C. Bulman Page Alexandra M. Z. Slawin Donald Westwood David J. Williams

P. C. B. Page, A. M. Z. Slawin, D. Westwood and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1989, 185 DOI: 10.1039/P19890000185

Dithiane

10.1039/p19890000185

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Citations (24)

Reactions of metallated 1,3-dithianes with carboxylic acid derivatives

Journal of the Chemical Society. Perkin transactions I/Journal of the Chemical Society. Perkin transactions. I (1988)

Philip C. Bulman Page Monique B. van Niel Donald Westwood

2-Lithio-1,3-dithianeand2-lithio-2-trimethylsilyl-l,3-dithianereactwithnitrilestoaffordprimaryaminoketene dithioacetals in good yields; these compounds exhibit marked ambident nucleophilicity. Use of other carboxylic acid derivatives as electrophiles normally produces acyl dithianes, however 2-lithio-2-trimethylsilyl-1,3-dithiane reacts with benzoyl cyanide to give a cyanoketene dithioacetal.

Trimethylsilyl

Trimethylsilyl cyanide

Dithiane

10.1039/p19880000269

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Citations (27)

Reaction between 2-lithio-1,3-dithiane and tetrahydrofuran: structure of bis[2-(1,3-dithianyl)]methanol

Acta Crystallographica Section C Crystal Structure Communications (1987)

Philip C. Bulman Page Derek J. Chadwick Monique B. van Niel Donald Westwood

Tetrahydrofuran

Dithiane

10.1107/s0108270187094010

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Citations (2)

Obituary

Anaesthesia (1974)

Ferguson Sybil ne'e Humphreys P. J. Helliwell Ji Young Lee T Dinnick D. Howat

Obituary

10.1111/j.1365-2044.1974.tb00743.x

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ChemInform Abstract: Diastereoselective Control of Enolate Alkylation in 2‐Acyl‐2‐alkyl‐1,3‐dithiane 1‐Oxides.

ChemInform (1990)

Philip C. Bulman Page Sukhbinder S. Klair Donald Westwood

Abstract Alkylation of the anti or syn acyl dithiane monosulfoxides (III) or (IV) leads to diastereomeric mixtures of the products (V) or (VII).

Dithiane

Diastereomer

10.1002/chin.199013208

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ChemInform Abstract: PYRIDIN-KATALYSIERTE UMSETZUNG VON ACYLCHLORIDEN MIT KALIUMCYANID IN WAESSRIGER LOESUNG

Chemischer Informationsdienst Organische Chemie (1971)

Donald Westwood R. K. Smalley

Bei der Umsetzung der o-substituierten Benzoylchloride (I) mit Kaliumcyanid in Gegenwart katalytischer Mengen an Pyridin entstehen in Ausbeuten von 20-50% die Dinitrile (II).

10.1002/chin.197104227

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Diastereoselectivity in the addition of grignard reagents to ketones controlled by the 1,3-dithiane 1-oxide asymmetric building block

Tetrahedron (1993)

Philip C. Bulman Page Jeremy C. Prodger Donald Westwood

Dithiane

Grignard reagent

Grignard reaction

10.1016/s0040-4020(01)80562-7

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Citations (31)

Chemistry of aminoketene dithioacetals: preparation of protected α-amino aldehydes and ketones and formation of nitrogen heterocycles

Journal of the Chemical Society Chemical Communications (1987)

Philip C. Bulman Page Monique B. van Niel Donald Westwood

The ambident anion (2) derived from primary aminoketene dithioacetal (1, R = Ph) reacts with alkyl halides at the carbon atom to give remarkably stable primary imines which may be reduced to give protected α-amino ketones using borane in quantitative yield, and under similar conditions aminoketene dithioacetal (1, R = Ph) gives the protected α-amino aldehyde (15); anion (2) reacts with the bis-electrophile epichlorohydrin to give the nitrogen heterocycle (9) in 80% yield, and other related chemistry is also reported.

Nitrogen atom

Primary (astronomy)

Boranes

Carbon fibers

Epichlorohydrin

10.1039/c39870000775

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Citations (21)

Diastereoselective control of enolate alkylation in 2-acyl-2-alkyl-1,3-dithiane 1-oxides

Journal of the Chemical Society. Perkin transactions I/Journal of the Chemical Society. Perkin transactions. I (1989)

Philip C. Bulman Page Sukhbinder S. Klair Donald Westwood

Stereochemical control of enolate alkylation in syn(5) and anti(4) acyl dithiane monosulphoxides has been investigated. The substrates were prepared in high yields from 2-substituted dithianes by acylation in two steps via the corresponding aldehydes followed by sulphoxidation. 2-Acyl-2-alkyl1,3-dithiane 1-oxides were readily deprotonated using a variety of bases. The enolates so generated reacted with methyl iodide and other alkylating agents to give diastereoisomeric mixtures of the alkylated products, the ratios observed being dependent upon the relative stereochemistry of the acyl dithiane oxide, the 2-alkyl substituent, and the base, solvent, and temperature used for the reaction. Diastereoselectivities sufficiently high that the minor isomer could not be detected by 1H n.m.r. spectroscopy at 250 MHz have been observed in some cases (Tables 2 and 3), the most selective system being the anti 2-acyl-2-ethyl derivative (4c). The data obtained fall into clear patterns which may be rationalized by proposing chelated chair-form transition states involving interaction of both the enolate and sulphoxide oxygen atoms with the metal counter-ions.

Dithiane

Methyl iodide

10.1039/p19890002441

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Citations (23)

ChemInform Abstract: Chemistry of Amino Ketene Dithioacetals: Preparation of Protected α‐Amino Aldehydes and Ketones and Formation of Nitrogen Heterocycles.

ChemInform (1987)

P. C. B. Page Monique B. van Niel Donald Westwood

Abstract The enamine (I) is transformed into the α‐methyl ketone (III) by lithiation, methylation, and subsequent hydrolysis.

10.1002/chin.198748217

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