13303-60-1

Upstream product

• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 1079-66-9 chloro-diphenylphosphine 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 21040-45-9 Cinnamyl acetate 
• 65567-06-8 lithium diphenylphosphide 
• 4392-24-9 Cinnamyl bromide 
• 4141-48-4 allyldiphenylphosphine oxide 
• 613-94-5 benzoic acid hydrazide 
• 300-57-2 allylbenzene 
• 4559-70-0 Diphenylphosphine oxide 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 829-85-6 diphenylphosphane 
• 191169-77-4 (1R,2R)-2-(Dimethylphenylsilyl)-3-diphenylphosphinoyl-1-phenylprop-1-yl tert-butyldimethylsilyl ether 

Downstream Products

• 165611-42-7 (1S,2R)-3-(diphenylphosphinoyl)-1-phenylpropane-1,2-diol 
• 165611-45-0 (1R,2S)-3-Diphenylphosphinoyl-1-phenylpropane-1,2-diol 
• 176242-43-6 (S)-(E)-3-Diphenylphosphinoyl-1-phenylprop-2-en-1-ol 
• 82679-76-3 tert-Butyl-diphenyl-[(1R,6R,7R,8S)-8-((2E,4E)-5-phenyl-penta-2,4-dienyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethoxy]-silane 

Relevant academic research and scientific papers

Studies on an Oxidative 1,4-Addition to s-trans-1,3-Dienes, a Key Reaction in a Strigol Total Synthesis

Oxidation of 4,6-heptadienoic acid systems with hydrogen peroxide in the presence of a catalytic amount of diphenyl diselenide leads to 5-(3-hydroxypropenyl)dihydrofuran-2-one systems with defined relative configuration at the 4 and 7 positions (carboxylic acid numbering). A system having a six-membered ring as part of the s-trans-diene system was an intermediate in a strigol total synthesis; a second system lacking the six-membered ring is the subject of the present publication. We accomplished a stereoselective synthesis of the diene system by (i) trapping a π-allyl palladium complex with lithium diphenylphosphinite to give an allylic diphenylphosphane oxide and (ii) a subsequent Horner-Wittig reaction. The species that brings about the oxidative 1,4-addition is benzeneperoxyseleninic acid. We also report observations that shed some light on the mechanism. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Alkenylation of C(sp3)?H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts

α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C?H zincation and copper-catalyzed C(sp3)?C(sp2) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.

Copper-catalyzed allylic C-H phosphonation

An efficient copper-catalyzed allylic C-H phosphonation reaction has been developed under mild reaction conditions. This method exhibits high regioselectivity and stereoselectivity. Various alkenes with useful functional groups are compatible in this tran

Palladium/copper-catalyzed oxidative arylation of terminal alkenes with aroyl hydrazides

An unprecedented oxidative arylation reaction of terminal alkenes with simple aroyl hydrazides has been developed under aerobic conditions for the stereoselective synthesis of 1,2-disubstituted alkenes. A range of aroyl hydrazides underwent palladium/copper-catalyzed oxidative Mizoroki-Heck reaction with terminal alkenes open to air in a 1:1 mixture of dimethyl sulfoxide and acetonitrile to give structurally diverse 1,2-disubstituted alkenes in moderate to excellent yields with excellent regio- and E-selectivity. The reaction tolerated a wide variety of functional groups, such as alkoxy, hydroxy, amino, fluoro, chloro, bromo, cyano, nitro, ester, amide, imide, phosphine oxide, and sulfone groups, and, moreover, molecular oxygen and dimethyl sulfoxide were demonstrated to serve as terminal oxidants. This study provides a useful method for the stereoselective synthesis of 1,2-disubstituted alkenes through direct transformation of the vinylic Ci-H bonds in terminal alkenes. Cross-coupling: An oxidative arylation reaction of terminal alkenes with simple aroyl hydrazides has been developed in the presence of a PdCl2/CuI catalyst under aerobic conditions to give a range of structurally diverse 1,2-disubstituted alkenes in moderate to excellent yields with excellent regio- and E-selectivity (see scheme; r.s.=regioselectivity).

Epoxysilanes as substrates in regio- and stereo-specific synthesis of silylated γ-hydroxyphosphane oxides, precursors of stereodefined allylphosphane oxides

Epoxysilanes experienced trans stereospecific α- or β-cleavage by the lithium derivative of methyldiphenylphosphane oxide leading to different compounds. The behaviour of the epoxysilanes towards this nucleophilic reagent depends on the nature of the sily

Diastereoselective nucleophilic additions to vinyl phosphine oxides

Some hydrogen, carbon, silicon, sulfur, nitrogen and oxygen nucleophiles react diastereoselectively with γ-oxygenated chiral vinyl phosphine oxides to give β-substituted phosphine oxides. Lithium N-benzyl-α-methylbenzylamide adds to prochiral vinyl phosphine oxides in the presence of trimethylsilyl chloride to provide, after protodesilylation, β-amino phosphine oxides as single diastereoisomers.

Asymmetric dihydroxylation of allylic phosphine oxides

Diphenylphosphinoyl diols have been produced by asymmetric dihydroxylation (AD) of allylic phosphine oxides and have been shown to be useful synthetic intermediates. The results of this study are discussed in terms of the model which has been proposed by Sharpless to explain the enantioselectivity of his AD reaction. The dihydroxylation results are thus of both mechanistic and synthetic value.

Diastereoselective reactions of optically active γ-substituted vinyl phosphine oxides

Dehydration of diphenylphosphinoyl diols (synthesised by asymmetric dihydroxylation of allylic phosphine oxides) gives γ-hydroxy vinyl phosphine oxides. Some diastereoselective reactions of vinyl phosphine oxides with hydrogen, carbon and heteroatomic nucleophiles are discussed.

Asymmetric dihydroxylations of allylic phosphine oxides

Allylic phosphine oxides 6 undergo asymmetric dihydroxylation to yield 1,2 diols 9. The enantioselectivity of these reactions depends critically on the class and quantity of chiral ligand used. A model to explain the sense and degree of asymmetric inducti