The total synthesis of (–)-phyllanthostatin-1

Smith, Amos B.; Hale, Karl J.; Vaccaro, Henry A.

doi:10.1039/c39870001026

Cited by 14 publications

(13 citation statements)

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“…Despite their potential use in synthesis, selective mixed diesterification and selective hydroxyl group protection/deprotection via esterification represent a challenge. By forming mixed esters, it is possible to selectively cleave one of the esters. − The regioselective formation of mixed diesters of diols in good yields, developed via the reaction of CKAs with carboxylic acids, is presented in this paper.…”

Section: Introductionmentioning

confidence: 99%

Selective Diesterification of Diols through Cyclic Ketene Acetal Intermediates

Stanley

Pittman

1999

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Selective Diesterification of Diols through Cyclic Ketene Acetal Intermediates

Stanley

Pittman

1999

J. Org. Chem.

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“…Additional work on the elimination kinetics of N,Ndimethylcarbamates led researchers to consider a generally accepted mechanism of a six-membered cyclic transition state similar to those described for acetates, carbonates and xanthates [1][2][3][4][5][6] [reaction (2)].…”

Section: Introductionmentioning

confidence: 99%

Kinetics of the homogeneous, unimolecular elimination reactions of ethyl oxamate, ethyl N,N‐dimethyloxamate and ethyl oxanilate in the gas phase

Chacin

Tosta

Herize

et al. 2004

J of Physical Organic Chem

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The gas‐phase elimination kinetics of the title compounds were determined over the temperature range 350–430°C and pressure range 35–240 Torr (1 Torr = 133.3 Pa). The reactions, which were carried out in a static reactor system, seasoned with allyl bromide and in the presence of a free radical inhibitor, are homogeneous, unimolecular and obey a first‐order rate law. The temperature dependences of the overall rate coefficients are given by the following Arrhenius equations: for ethyl oxamate, log [k1 (s−1)] = (13.28 ± 0.20) – (203.7 ± 2.5) kJ mol−1 (2.303RT)−1, for ethyl N,N‐dimethyloxamate, log [k1 (s−1)] = (13.06 ± 0.34) – (206.8 ± 4.4) kJ mol−1(2.303RT)−1, and for ethyl oxanilate, log [k1 (s−1)]= (13.86 ± 0.12)–(207.4 ± 1.5) kJ mol−1(2.303RT)−1. The overall rates, the partial rates and the kinetic and thermodynamic parameters of these eliminations are presented and discussed. These reactions appear to proceed through moderately polar cyclic transition states. Copyright © 2004 John Wiley & Sons, Ltd.

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“…The mechanism of the N-dealkylation of N-dimethylanilines catalyzed by heme enzymes and their analogs has attracted considerable attention. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Iodosylbenzene (C 6 H 5 IO) catalyzed by tetraphenylporphyrinatoiron(III) chloride [Fe(III)TPPCl] 12 oxidizes N,N-dimethylbenzylamines by an initial electron transfer (ET) process. The reactions indicate a small negative r value ( = À0.41) for Fe(III)TPPCl and marginal intermolecular kinetic isotope effect (KIE), k H /k D = 1.3 with PhCH 2 NMe 2 and PhCD 2 NMe 2 .…”

Section: Introductionmentioning

confidence: 99%