scispace - formally typeset
Search or ask a question
Author

Bryan M. Gatehouse

Bio: Bryan M. Gatehouse is an academic researcher from Monash University, Clayton campus. The author has contributed to research in topics: Crystal structure & Denticity. The author has an hindex of 21, co-authored 92 publications receiving 1346 citations.


Papers
More filters
Journal ArticleDOI
TL;DR: In this article, the reaction of N-acyl isatide with dimethylmalonyl dichloride yielded the oxazinoindole (6) rather than the expected product.
Abstract: Reaction of sodium isatide with dimethylmalonyl dichloride yielded the oxazinoindole (6) rather than the expected product (4). The glyoxylamide (8), which served as a precursor to the macrocyclic complex (15), was therefore prepared by a sequence involving compounds (9), (10) and (7). Such a route makes use of the reactivity of N-acyl isatins and the protecting capacity of the benzyloxycarbonyl group. The structure of compound (6) was established by X-ray crystallography.

2 citations

Journal ArticleDOI
TL;DR: The oxazinoindoletrione (3) and trione (4, 5, 6, 7, 8, 9, 10) were all established by X-ray crystallography.
Abstract: The oxazinoindoletrione (3) underwent reaction with aqueous ammonia in methanol or ethanol to yield the polycyclic methyl or ethyl esters (4) and (5) respectively. Reaction of trione (3) with gaseous ammonia in dry ethanol gave the aminobenzodiazepinone (7). This compound lost ammonia on heating in toluene to give compound (11) and in the presence of methanol or ethanol gave the methyl or ethyl esters (9) and (10) respectively. The structures of compounds (4), (7) and (10) were all established by X-ray crystallography.

2 citations

Journal ArticleDOI
TL;DR: In this article, the stereochemistry of the minor dimer is established, contrary to theoretical predictions, as the exo-isomer of the 8.8,8-Dimethylisobenzoefvene.
Abstract: 8,8-Dimethylisobenzofulvene undergoes spontaneous cyclo-dimerization to give a mixture of two isomers of composition C24H24, The minor isomer crystallizes in the orthorhombic space group Pbca with a 16.815(8), b 16.975(8) and c 13.058(6)A pobs 1.13(3)g cm-3, pealc 1.13 g cm-3 for Z 8. The structure was solved from diffractometer data by direct methods and was refined by full-matrix least squares to final residuals R 0.040, Rw 0.046 for 885 observed data. The stereochemistry of the minor dimer is established, contrary to theoretical predictions, as the exo-isomer. There is evidence of intramolecular steric strain particularly demonstrated by the elongated C-C single bonds, 1.590(7) and 1.570(7) A, which are formed in the dimerization process.

2 citations

Journal ArticleDOI
TL;DR: In this paper, the free energy of activation at 268 K was estimated to be 56'±'8'kJ for the E-3-amino-2-benzoyl-2butenoate.
Abstract: Ethyl-3-amino-2-benzoyl-2-butenoate crystallizes from pentane as either the E (mp 82–84 °C) or the Z-isomer (mp 95.5–96.5 °C). The E isomer is less stable, and changes spontaneously into the Z, which bas been identified by X-ray crystallography. The structure is characterised by an N–H/ester CO hydrogen bond and a very long C2—C3 bond (1.39 A). Nuclear magnetic resonance methods have been used to measure the rate of isomerization at several temperatures, leading to the estimate that the free energy of activation at 268 K is 56 ± 8 kJ.

2 citations


Cited by
More filters
Journal ArticleDOI
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Abstract: In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

2,268 citations

Journal ArticleDOI
TL;DR: In this paper, the preparation of a colloidal colloidal by un procede sol gel is described, and a procedure for determination des proprietes electriques et electrochimiques is described.

2,040 citations

Journal ArticleDOI
TL;DR: The power of cascade reactions in total synthesis is illustrated in the construction of complex molecules and underscore their future potential in chemical synthesis.
Abstract: The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

1,762 citations

Journal ArticleDOI
TL;DR: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which has yet to be eclipsed by any other transformation in the current synthetic repertoire as mentioned in this paper.
Abstract: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

1,427 citations