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Larry E. Brammer

Bio: Larry E. Brammer is an academic researcher from University of Florida. The author has contributed to research in topics: Ring strain & Allylic rearrangement. The author has an hindex of 7, co-authored 10 publications receiving 216 citations.

Papers
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TL;DR: In this article, several synthetic pathways to cyclohex-5-ene-1R,2S,3R,4R-tetrol (conduritol C) and cycloencoderhex-1S,2R, 3R, 4R, 6R, 7R, 8R, 9R, 12R, 14R, 15R, 16R, 17R, 18R, 19R, 20R, 21R, 22R, 23R, 24R, 25R, 26R, 27R, 28R,

91 citations

Journal ArticleDOI
TL;DR: In this article, a multigram scale starting with bromobenzene in seven steps by three different cis-dihydroxylations (enzymatic, OsO 4 and RuO 4 catalyzed) employed in tandem.

36 citations

Journal ArticleDOI
TL;DR: Fully stereoselective large-scale syntheses have been attained for l - chiro -inositol (2 ) and muco -inotol (3 ) by means of controlled peripheral oxygenation of cyclohexadiene diol as mentioned in this paper.
Abstract: Fully stereoselective large-scale syntheses have been attained for l - chiro -inositol ( 2 ) and muco -inositol ( 3 ) by means of controlled peripheral oxygenation of cyclohexadiene diol 1 .

31 citations

Journal ArticleDOI
TL;DR: In this article, the effect of radical-stabilizing substituents (phenyl and vinyl) on the ring opening of arylcyclopropylketyl anions was examined.
Abstract: Aryl cyclopropyl ketones have frequently been used as probes for single-electron transfer in organic reactions. The implicit assumption in these studies is that upon one-electron reduction, the corresponding arylcyclopropylketyl anions will undergo ring opening in analogy to the cyclopropylcarbinyl free radical. Earlier work in our laboratory has shown that ring opening of arylcyclopropylketyl anions is kinetically and thermodynamically unfavorable when the only substituents on the cyclopropane ring are alkyl or H. This sluggishness is attributable to a loss of resonance energy upon ring opening which is not fully compensated by the reliefofcyclopropane ring strain. Consequently, aryl cyclopropyl ketones are unsuitable probes for single-electron transfer. In this paper, we examine the effect of radical-stabilizing substituents (phenyl and vinyl) on the ring opening of arylcyclopropylketyl anions.

24 citations

Journal ArticleDOI
TL;DR: Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology.
Abstract: Several vinyl halides previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the...

23 citations


Cited by
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Journal ArticleDOI
TL;DR: In this paper, a critical review of conversion constants amongst various reference electrodes reported in the literature reveals that in most cases the comparisons of redox potential values are far from accurate, and therefore, caution should be exercised when one is comparing the redox properties of complexes measured in CH 3 CN solutions versus different reference electrodes.

1,212 citations

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TL;DR: In this article, the effect of the E Factor concept has had over the last fifteen years on developments in the chemical industry and pharmaceutical industry with regard to waste minimisation and to assess its current status in the broader context of green chemistry and sustainability.

1,206 citations

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TL;DR: The fundamental concepts underlying the principles of green and sustainable chemistry--atom and step economy and the E factor--are presented, within the general context of efficiency in organic synthesis, and the transition from fossil-based chemicals manufacture to a more sustainable biomass-based production is discussed.
Abstract: In this tutorial review, the fundamental concepts underlying the principles of green and sustainable chemistry - atom and step economy and the E factor - are presented, within the general context of efficiency in organic synthesis. The importance of waste minimisation through the widespread application of catalysis in all its forms – homogeneous, heterogeneous, organocatalysis and biocatalysis – is discussed. These general principles are illustrated with simple practical examples, such as alcohol oxidation and carbonylation and the asymmetric reduction of ketones. The latter reaction is exemplified by a three enzyme process for the production of a key intermediate in the synthesis of the cholesterol lowering agent, atorvastatin. The immobilisation of enzymes as cross-linked enzyme aggregates (CLEAs) as a means of optimizing operational performance is presented. The use of immobilised enzymes in catalytic cascade processes is illustrated with a trienzymatic process for the conversion of benzaldehyde to (S)-mandelic acid using a combi-CLEA containing three enzymes. Finally, the transition from fossil-based chemicals manufacture to a more sustainable biomass-based production is discussed.

1,095 citations

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TL;DR: The optimisation of enzyme properties using in vitro evolution and improvement of their operational stability by immobilisation as cross-linked enzyme aggregates (CLEA) are presented and the biocatalytic aerobic oxidation of starch to carboxy starch is presented as an example of green chemistry in optima forma i.e. a biocompatible product from a renewable raw material using a biocesealytic air oxidation.

737 citations