115346-88-8

Upstream product

• 37868-70-5 5-phenyl-pent-2-enal 
• 115346-89-9 5-phenyl-1,3-bis(trimethylsiloxy)pentane 
• 104-53-0 3-phenyl-propionaldehyde 
• 588731-94-6 (2E,5S)-5-hydroxy-7-phenyl-2-heptenoic acid ethyl ester 
• 261159-45-9 (R)-4-(2-phenylethyl)oxetane-2-one 
• 115404-93-8 (2R,6S,7S,10R)-7-Isopropyl-10-methyl-2-phenethyl-1,5-dioxa-spiro[5.5]undecane 
• 115404-97-2 5-phenyl-pentane-1,3-diol 
• 53376-62-8 ethyl 3-hydroxy-5-phenylpentanoate 

Relevant academic research and scientific papers

Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides

We have developed an unprecedented highly enantioselective catalytic peroxidation of enals. Critical to this development is the discovery that varying the structure of the hydroperoxide has a significant impact on the enantioselectivity of the organocatal

Lewis base activation of Lewis acids. Vinylogous aldol reactions

A highly regioselective vinylogous aldol reaction catalyzed by SiCl4 and a chiral phosphoramide (R,R)-5, providing δ-hydroxy enones for a variety of aldehyde and dienol ether structures, has been developed. Low catalyst loadings (1 mol %) can b

Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

[reaction: see text] The utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported. Titanium(IV) chloride, along with (-)-sparteine and N-methylpyrrolidinone, is employed for enolization. Subsequent a

Stereoselective Acetalization of 1,3-Alkanediols by l-Menthone: Application to the Resolution of Racemic 1,3-Alkanediols and to the Determination of the Absolute Configuration of Enantiomeric 1,3-Alkanediols

A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described.Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4.The two can be readily separated by silica gel column chromatography.Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol.An empirically derived correlation of configuration and 1H NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation.The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

RESOLUTION OF 1,3-ALKANEDIOLS VIA CHIRAL SPIROKETALS DERIVED FROM l-MENTHONE

Ketalization reaction of racemic 1,3-alkanediols with l-menthone gave a mixture of diastereomeric spiroketals that was easily separated by silica gel column chromatography and converted into enantiomerically pure diols by acid-catalyzed hydrolysis.

AN ENANTIODIFFERENTIATING CONVERSION OF RACEMIC 1,3-ALKANEDIOLS INTO ENANTIOMERICALLY PURE MATERIALS

Titanium tetrachloride promoted ring-cleavage reaction of a mixture of diastereomeric spiroketals derived from racemic 1,3-alkanediols and l-menthone, followed by benzoylation by Mitsunobu reaction, and the subsequent hydrolysis gave enantiomerically pure 1,3-alkanediols.