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and stereoselective 1,4-hydroboration of 1,3-dienes.

Complexation of the dienophile with a protic or Lewis acid has dramatic effects on many Diels-Alder cycloadditions. Rates of reaction are increased by factors as large as 106, the preference for endo stereoselectivity is increased, and the ortho-para selectivity may also be higher. This is a consequence of the lowering of the LUMO of the dienophile by the increased electron deficiency caused by the Lewis acid, and changes in the orbital coefficients which cause stronger secondary orbital interactions and larger regiochemical preference. There are also downsides to adding Lewis or protic acids - poluymerization or other decomposition reactions may be accelerated also.

A highly efficient chemo-, regio-, and stereoselective synthesis of (7E,9Z)-dodecadien-1-yl acetate, a sex pheromone of Lobesia botrana, via a functionalized organoborate.

1,3-Diene synthesis by or C-C coupling - Organic …

1,2-diamine synthesis by diamination - Organic chemistry

Stereoselective synthesis of (2E,4Z)-dien-1-ols; key intermediates for synthesis of sex pheromones of silk worm and of grape vine moth.

An efficient method for the construction of Csp2-Csp3 bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks.

N2 - An efficient method for the construction of Csp2-Csp3 bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks.

1,2-Amino Alcohols and Their Heterocyclic Derivatives …

AB - An efficient method for the construction of Csp2-Csp3 bond in a regio- and stereoselective fashion involving 1,3-terminal dienes, enol triflates/nonaflates, and sodium formate under Pd(0)-catalysis is described. The three component assembly allows trapping of a π-allyl intermediate, after the initial migratory insertion of the diene, by a hydride source that leads to structurally complex and synthetically challenging tri- and tetrasubstituted alkene building blocks.

Sharpless, Asymmetric Dihydroxylation of Primary Alloylic Halides and a Concise Synthesis of (-)-Diepoxybutane, , 35, 3469 (1994)

Regioselective Synthesis of 4-Alkylpyridines From Pyridine And Aldehydes via Dipole Reversal Process of 1,4-Dihydropyridine Phosphonate, 2006,

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Dr. M. Jeganmohan Group - IISER Pune


Matta Lab.: Publications - 東京理科大学

Indium-Mediated 1,2,4,5-Hexatetraen-3-ylation of 4-Acetoxy-2-azetidinones and Their Applications to the Diels-Alder Reactions for the Synthesis of 2-Azetidinone Derivatives, 2008,

Asymmetric Total Syntheses of Colchicine, β …

Stereoselective Synthesis of 4-Alkyl- or 4-Aryl-3-ethoxycarbonyl-2-halo-1,3-dienes from the Reaction of Allenols Having Ethoxycarbonyl Group with Indium Trihalide, 2009,

K. Barry Sharpless -- Publications

Abstract: Infrared irradiation promoted the Diels-Alder cycloadditions of exo-2-oxazolidinone dienes 1–3 with the Knoevenagel adducts 4–6, as dienophiles, leading to the synthesis of new 3,5-diphenyltetrahydrobenzo[d]oxazol-2-one derivatives (7, 9, 11 and 13–17), under solvent-free conditions. These cycloadditions were performed with good regio- and stereoselectivity, favoring the para-endo cycloadducts. We also evaluated the one-pot three-component reaction of active methylene compounds 20, benzaldehydes 21 and exo-2-oxazolidinone diene 2 under the same reaction conditions. A cascadeInt. J. Mol. Sci. 2012, 13 2591 Knoevenagel condensation/Diels-Alder cycloaddition reaction was observed, resulting in

2-octanone, 111-13-7 - The Good Scents Company

Highly Selective Synthetic Method of 1,6-Diols Having Enynes: Development of 3,6-Dianion Reagent of 1,2-Hexadiene-4-yne Using 1,6-Dibromo-2,4-hexadiyne and Indium, 2007,

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