140631-03-4

Upstream product

• 135414-95-8 (1R,2S)-1-phenyl-3-butene-1,2-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 82238-14-0 (1R,2R)-2-(1-Methoxy-1-methyl-ethoxy)-1-phenyl-but-3-en-1-ol 
• 100-52-7 benzaldehyde 
• 77896-99-2 2-<(Z)-3-(1-methoxy-1-methylethoxy)-2-propenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 19261-14-4 1-phenylbut-3-ene-1,2-diol 
• 104516-09-8 1-phenylbuta-2,3-dien-1-ol 
• 140438-80-8 (1R,2S)-2-(4'-methoxyphenoxy)-1-phenyl-1-(trimethylsiloxy)-3-butene 
• 139284-73-4 (1R,2S)-2-(4'-methoxyphenoxy)-1-phenyl-3-buten-1-ol 
• 474958-71-9 (1R,2S)-2-(methoxyethoxymethoxy)-1-phenylbut-3-enyl 4-nitrobenzoate 
• 474958-72-0 (1R,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenylbut-3-en-1-ol 
• 474958-70-8 (1S,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenyl-but-3-en-1-ol 

Downstream Products

• 130718-77-3 (4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde 
• 473543-38-3 (1S)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol 

Relevant academic research and scientific papers

3-Bromopropenyl esters in organic synthesis: Indium- and zinc-mediated entries to alk-1-ene-3,4-diols

Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-l-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereo-selectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.

Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis

A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.

Total synthesis of (±)-9-deoxygoniopypyrone. Application of the iodocyclofunctionalization reaction of α-allenic alcohol derivatives

The synthesis of (±)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 5 is described. Iodocyclofunctionaliztion of the N-tosyl carbamate derivative of 5 using I2 and Ag2CO3 provided, in a highly diastereoselective and r

Total Synthesis of (+/-)-9-Deoxygoniopypyrone

The total synthesis of (+/-)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 2 is described.The synthesisis accomplished in 10 steps with the relative configuration of the three contiguous asymmetric centers being established by the highly diastereose

Enantioselective allyltitanation of aldehydes with cyclopentadienylialkoxyallylitanium complexes

The preparation, analysis, and reactions of novel, highly stereoselective cyclopentadienyldialkoxyallyltitanium reagents, available in both enamiomeric forms, are described. Chiral monochlorotitanates are readily prepared from CpTiCl3 or Cp*TiC

Stereoselective Synthesis of Alcohols, XX. - Diastereoselective Addition of γ-Alkoxyallylboronates to Aldehydes

Both the (Z)- and (E)-γ-alkoxysubstituted allylboronates 1 and 3 have been prepared.They add to aldehydes with a diastereoselectivity generally exceeding 90percent to give the syn-(2) and anti-diol derivatives 4, respectively.The structure of one of these adducts has been established by conversion into exo-brevicomin (26).