21939-45-7

Upstream product

• 6783-05-7 trans-2-phenylvinylboronic acid 
• 107-21-1 ethylene glycol 
• 100-42-5 styrene 
• 14559-94-5 2-vinyl-[1,3,2]dioxaborolane 
• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 100-52-7 benzaldehyde 

Downstream Products

• 93-56-1 phenylethane 1,2-diol 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 1011295-48-9 (4S,5R,E)-1-benzyl-4-hydroxy-5-styrylpyrrolidin-2-one 
• 1011295-37-6 (4S,5S,E)-1-benzyl-4-hydroxy-5-styrylpyrrolidin-2-one 
• 136981-81-2 (R)-(E)-1,3-diphenyl-prop-2-en-1-ol 
• 132014-29-0 (S)-(E)-1,3-diphenylprop-2-en-1-ol 

Relevant academic research and scientific papers

Factors affecting the efficiency and stereoselectivity of α-amino acid synthesis by the Petasis reaction

The use of chiral secondary amines containing only one branched substituent has been shown to give optimal yields and stereoselectivities in the preparation of α-amino acids using the Petasis reaction. While the use of chiral primary amines generally give

Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro- 1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of onychomycosis

A structure-activity relationship investigation for a more efficacious therapy to treat onychomycosis, a fungal infection of the toe and fingernails, led to the discovery of a boron-containing small molecule, 5-fluoro-1,3-dihydro- 1-hydroxy-2,1-benzoxaborole (AN2690), which is currently in clinical trials for onychomycosis topical treatment.

New catalytic route to functionalized vinylboronates

Vinylsubstituted boronates i.e. vinyldioxaborolane and vinyldioxaborinane react regioselectively with olefins in the presence of RuHCl(CO)(PCy 3)2 with the formation of functionalized vinylboron derivatives. The reaction opens a new catalytic route for preparation of organoboranes. The Royal Society of Chemistry 2005.

Lithium bis(ethylenedioxyboryl)methide and its reactions with carbonyl compounds and with the chlorotriphenyl derivatives of germanium, tin and lead

Transesterification of tris(dimethoxyboryl)methane, HC[B(OCH3)2]3, with ethylene glycol yielded tris(ethylenedioxyboryl)methane (I), HC(BO2C2H4)3 which with methyllithium in THF at -70°C precipitated lithium bis(ethylenedioxyboryl)methide (II), Li+ HC(BO2C2H4)2-. Reaction of II with Ph3MCl, where M = Ge, Sn, or Pb, gave Ph3MCH(BO2C2H4)2. The analogous 1,3-propanediol ester, Li+HC(BO2C3H6)2-, yielded Ph3MCH(BO2C3H6)2. Treatment of Ph3SnCH(BO2C2H4)2 with MeLi followed by Ph3SnCl gave (Ph3Sn)2CHBO2C2H4, showing that one B and one Sn atom are sufficient to stabilize a carbanion. Reaction of II with aldehydes gave high yields of 1-alkene-1-boronic esters, RCHCHBO2C2H4, with unexpectedly high stereoselectivity, 90-100% trans by NMR analysis. Aqueous work-up of these boronic esters yielded the boronic acids, RCHCHB (OH)2, which crystallized as the pure trans isomers. Ketones react with II in an analogous manner. The reaction with acetophenone was not stereospecific. Functional group compatibility has been demonstrated in condensations of II with 1,3-dichloroacetone, cinnamaldehyde, p-nitrobenzaldehyde, and p-dimethylaminobenzaldehyde. The trans geometry of the major isomer of CH3CHCHBO2C2H4 was proved by B-butylation with butyllithium followed by rearrangement with iodine and base to form cis-2-heptene, a sequence of known stereochemistry, and analogous structure proofs were carried out with cis-CH3CHCHBO2C2H4 and trans-C6H5CHCHBO2C2H4.