158703-50-5

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 55985-68-7 3-bromo-4-phenylbutan-2-one 
• 1373825-02-5 (2S,3S)-4-phenyl-3-chloro-2-butanol 
• 53973-14-1 (Z)-3-chloro-4-phenyl-3-buten-2-one 
• 1896-62-4 (E)-benzalacetone 
• 22965-96-4 (Z)-3-bromo-4-phenyl-3-buten-2-one 
• 160189-76-4 (2S,3S)-4-phenyl-3-bromo-2-butanol 

Downstream Products

• 167255-77-8 (+)-(2S,3S)-3-azido-4-phenyl-2-butanol 
• 701-70-2 (S)-1-phenylbutan-2-ol 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 158703-59-4 (-)-(2R,3S)-2-methyl-3-benzylaziridine 

Relevant academic research and scientific papers

On the baker's yeast mediated transformation of α-bromoenones. Synthesis of (1S,2R)-2-bromoindan-1-ol and (2s,3s)-3-bromo-4-phenylbutan-2- ol

Fermenting baker's yeast converts α-bromo substituted enones 7 and 10 into enantiomerically pure (1S,2R)2-bromoindan-1-ol 3 and (2S,3S)-3-bromo-4- phenylbutan-2-ol 11, respectively, through the intermediacy of the corresponding saturated ketones. Structurally related 16 provides the (2R)- allylic alcohol 17 prevalently.

Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis

Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox 1010 and 1076 were also used to inhibit the electron transfer mechanism. The obtained halohydrins are important chiral building blocks to obtain optically active epoxides and aminoalcohols.

Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3- epoxybutane and 1-phenyl-1,2-epoxypropane

All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2- epoxypropane (β-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.