6124-79-4Relevant academic research and scientific papers
Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration
Deangelis, Andrew,Dmitrenko, Olga,Fox, Joseph M.
supporting information; experimental part, p. 11035 - 11043 (2012/08/28)
Intermolecular Rh-catalyzed reactions of cyclic α-diazocarbonyl compounds with chemoselectivity over β-hydride elimination are described. These methods represent the first general intermolecular reactions of Rh-carbenoids that are selective over tertiary
Asymmetric Synthesis of a Key Synthetic Precursor for (+)-Strigol and Sorgolactone
Schroeer, Josef,Welzel, Peter
, p. 6839 - 6858 (2007/10/02)
En-route to non-racemic iodomethyl butyrolactone 23g a number of stereoselective 1,4-additions and reductions have been studied.The only satisfactory approach involved baker's yeast reduction (21c->23c) as key step.
Regioselectivity control in metal hydride reductions of substituted maleic anhydrides
Kayser, Margaret M.,Breau, Livain,Eliev, Sonia,Morand, Peter,Ip, H. S.
, p. 104 - 109 (2007/10/02)
A systematic study of reductions of unsymmetrically substituted maleic anhydrides by a variety of metal hydride reagents indicates that the high regioselectivity observed in these reactions is controlled chiefly by electronic factors.
A NEW CONVENIENT LABORATORY SYNTHESIS OF TRIMETHYLSILYL BROMIDE
Bellassoued, M.,Borgi, A. El,Gaudemar, M.
, p. 973 - 976 (2007/10/02)
Trimethylsilyl bromide is prepared in a laboratory scale from trimethylsilyl 4-bromo 2-alkenoates in almost quantitative yield.
Reversal of Regioselectivity in the Reduction of gem-Disubstituted Cyclic Carboxylic Acid Anhydrides
Morand, Peter,Salvator, Judith,Kayser, Margaret M.
, p. 458 - 459 (2007/10/02)
The regioselective partial reduction of gem-disubstituted cyclic carboxylic acid anhydrides to the corresponding γ-lactones with LiAlH4 or NaBH4 is almost completely reversed when potassium tri-s-butylborohydride is used as the reducing agent.
The Preparation of Synthetic Analogues of Strigol
Johnson, Alan W.,Gowda, Gopala,Hassanali, Ahmed,Knox, John,Monaco, Sam,et al.
, p. 1734 - 1743 (2007/10/02)
A range of analogues of the natural germination stimulant, strigol, for parasitic weeds of the genera Striga and Orobanche, has been prepared.Most of the products contain an α-formyl-γ-lactone (or α-formyl-γ-lactam) grouping attached through an enol-ether linkage to the 5-position of a but-2-enolide.Some have shown sufficiently high activities as to warrant large-scale field trials.
Regioselectivity of metal hydride reductions of unsymmetrically substituted cyclic anhydrides. Systems where "steric hindrance along the preferred reaction path" rationalization is not applicable
Kayser, Margaret M.,Morand, Peter
, p. 2484 - 2490 (2007/10/02)
Metal hydride reductions of planar cyclic anhydrides such as methylmaleic or 3-substituted phthalic anhydrides occur preferentially at the sterically more hindered carbonyl function.This regioselectivity cannot be rationalized in terms of "the most favourable pathway for non-perpendicular attack by a nucleophile" since both carbonyl groups present are equally accessible to non-perpendicular approach.A study which takes into account the alkaline cation and inductive, mesomeric, and steric effects has been conducted for the reduction of several conjugated and aromatic anhydrides.A qualitative interpretation for the regioselectivities observed in these reductions (as well as in reductions already reported in the literature) is suggested.An early transition state for the catalyzed versus late transition state for the non-catalyzed process is proposed.
