ORCID Profile
0000-0003-1692-3646
Current Organisation
University of Nottingham
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Publisher: Wiley
Date: 05-02-2016
Abstract: A highly stereoselective route to functionalized pyrrolidines by the metal-catalyzed erted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N-H insertion but is erted by an intermolecular aldol reaction.
Publisher: Elsevier BV
Date: 2013
Publisher: American Chemical Society (ACS)
Date: 18-11-2010
DOI: 10.1021/JO101691N
Abstract: A total synthesis of (+)-cymbodiacetal (1) has been completed from (R)-(+)-limonene oxide using a hetero-Diels-Alder cycloaddition as a key step. The key Diels-Alder cycloaddition proceeds with endo-selectivity (2:1, endo/exo) in quantitative yield, and the two diastereomeric spirochroman products are isolable, stable products. Furthermore, the exo- and the endo-hetero-Diels-Alder cycloaddition products (2 and 7) can be oxidized with m-CPBA to produce (+)-cymbodiacetal (1) and the C(2)-symmetric bis-hemiacetal structure 8, respectively. The isomeric hemiacetal 9 is produced in both oxidation reactions. The structures of (+)-cymbodiacetal (1), its C(2)-symmetric diastereoisomer 8, and the isomeric hemiacetal 9 were confirmed using X-ray crystallography.
Publisher: American Chemical Society (ACS)
Date: 21-09-2001
DOI: 10.1021/OL016603C
Abstract: [reaction: see text]. The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with >95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.
Publisher: Wiley
Date: 09-06-2015
Abstract: Copper- or rhodium-catalyzed reactions of diazocarbonyl compounds with β-hydroxyketones give highly substituted tetrahydrofurans with excellent diastereoselectivity. Under mild conditions, the single-step process starts as a carbene O-H insertion reaction, but is erted by an intramolecular aldol reaction.
Publisher: Elsevier BV
Date: 10-1992
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7OB02204B
Abstract: The total synthesis of aritasone via the proposed biosyntheic hetero-Diels–Alder [4 + 2] cyclodimerisation of pinocarvove, has been achieved under ultra-high pressure (19.9 kbar) conditions.
Publisher: American Chemical Society (ACS)
Date: 05-10-2002
DOI: 10.1021/JO025892V
Abstract: An enantioselective synthesis of the alpha,alpha-dialkyl-alpha-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C5SC03463A
Abstract: We report the first synthesis of taxadiene-4(5)-epoxide, which rearranges upon acid treatment to produce products of relevance to taxol biosynthesis.
Publisher: American Chemical Society (ACS)
Date: 21-02-2008
DOI: 10.1021/JO7027695
Abstract: An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester.
Publisher: Royal Society of Chemistry (RSC)
Date: 1999
DOI: 10.1039/A902411E
Location: United Kingdom of Great Britain and Northern Ireland
No related grants have been discovered for Christopher J. Hayes.