115276-20-5

Upstream product

• 4894-75-1 1-phenyl-4-cyclohexanone 
• 50622-10-1 (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol 
• 126325-72-2 2,4-dihydroxy-4-phenylcyclohexanedione (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 69125-55-9 4-hydroxy-1-methoxy-1-cyclohexene 
• 126325-70-0 2,4-dihydroxycyclohexanone (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 126325-71-1 2-hydroxy-1,4-cyclohexanedione 1-<(2S,3S)-1,4-dimethoxy-2,3-butylene>acetal 
• 126325-69-7 2,4-dihydroxycyclohexanone dimethylacetal 

Downstream Products

• 115276-23-8 2R-2-hydroxy-4-phenyl-3-cyclohexen-1-one (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 115276-23-8 2S-2-hydroxy-4-phenyl-3-cyclohexen-1-one (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 
• 115276-23-8 2-hydroxy-4-phenyl-3-cyclohexen-1-one (2S,3S)-1,4-dimethoxy-2,3-butylene acetal 

Relevant academic research and scientific papers

Asymmetric Synthesis Using Chiral Acetals: Highly Stereoselective Reduction of Chiral α-Keto-β,γ-unsaturated Acetals and Its Application for the Synthesis of (R)-(-)- and (S)-(+)-3'-Methoxy-4'-O-methyljoubertiamine

Reduction of the chiral α-keto-β,γ-unsaturated acetals (1) derived from (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol was studied.Extremily high stereoselectivity was attained with LiAlH4 and two epimeric allyl alcohols (2aA-2cA and 2aB-2cB) were prepared selectively by a proper choice of additive.As an application of this methodology, total syntheses of (R)-(-)-3'-methoxy-4'-O-methyljoubertiamine and its enantiomer were achieved from the single chiral enone acetal (3) through a highly stereocontrolled reduction followed by the Claisen-Eschenmoser rearrangement.

HIGHLY STEREOSELECTIVE REDUCTION OF CHIRAL α-KETO-β,γ-UNSATURATED ACETALS: SYNTHESIS OF BOTH EPIMERIC ALLYL ALCOHOLS BY PROPER CHOICE OF ADDITIVE

Highly stereoselective reduction of chiral α-keto-β,γ-unsaturated acetals (1a-3a) into each two epimeric optically active allyl alcohols (1b-3b and 1c-3c) was attained by LiAlH4 using additive (LiBr, MgBr2).