88292-43-7

Upstream product

• 88002-15-7 Phenylglyoxylsaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)-1-cyclohexyl>ester 
• 611-71-2 (R)-Mandelic Acid 
• 65253-04-5 (-)-8-phenylmenthol 
• 161634-63-5 (-)-(1R,3R,4S)-8-phenylmenthyl 2-diazo-2-phenylacetate 
• 19040-53-0 Trimethylphenyllead 
• 108794-12-3 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate 
• 603-33-8 triphenylbismuthane 
• 611-73-4 Benzoylformic acid 

Downstream Products

• 14467-49-3 (R)-(-)-α-<<(1-methylethyl)amino>methyl>benzenemethanol 
• 14467-53-9 (S)-(+)-2-(-amino)-1-phenylethanol 
• 89843-14-1 2-hydroxy-N-isopropyl-2-phenylacetamide 

Relevant academic research and scientific papers

Rhodium-catalyzed reactions of arylbismuth and aryllead reagents with a chiral glyoxylate hydrate in air and water: Water-promoted diastereoselectivity enhancement

In the presence of a rhodium catalyst, a chiral glyoxylate hydrate reacts with arylbismuth and aryllead reagents in water and under an atmosphere of air to give the corresponding addition products in high yields. The diastereoselectivities of the reactions were dramatically improved by using water as the solvent.

Diastereoselective reduction and carbon-carbon bond formation of α-keto esters/amides with SmI2

The stereoselective reduction of α-keto esters/α-keto amides, which have various chiral auxiliaries using SmI2, is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)- and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries

Diastereoselectivity in the O-H insertion reactions of carbenoids derived from phenyldiazoacetates of chiral alcohols. II comparison of rhodium(II)- and acid-mediated reactions

Rhodium(II)- or acid-mediated decomposition of 2-diazo-2-phenylacetates of chiral alcohols in the presence of various hydroxylic compounds (ROH) results in the diastereoselective formation of 2-hydroxy-, 2-alkoxy- or 2-trialkylsiloxy-2-phenylacetateSj with the acid-mediated process giving the higher diastereoselectivity.

Diatereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of α-Hydroxy and α-Alkoxy Esters

A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)-menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)-10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding α-keto esters 1 by way of the tosylhydrazones 2.Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity.A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results.The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration.Possible mechanisms are discussed.

Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary

(1R,4aS,8S,8aS)-8-(5'-Methoxy-2'-methylphenyl)-8-methyldecahydro-1-nap hthalenol 3a is a highly efficient chiral auxiliary in the Diels-Alder addition of its acrylate ester 5 and in the DIBAL-H and Grignard reactions of its phenylglyoxylate ester 7.

DIASTEREOSELECTIVE REDUCTION OF AN α-KETO-ESTER DERIVED FROM (-)-8-PHENYLMENTHOL: A 4-step synthesis of R-Halostachine analogue

An efficient (80percent total yield) 4-step synthesis of 94percent e.e.R-(-)-Halostachine analogue is described.The method offers the possibility to introduce various substituents onto the aromatic ring and various alkyl groups on the amine.A one-step and high yield (ca.100percent) conversion of esters into amides is presented.

Asymmetric Induction. Reduction, Nucleophilic Addition to, and Ene Reactions of Chiral α-Ketoesters

Ketoesters of 8-phenylmenthol undergo reduction with potassium tri-isopropoxyborohydride, addition of Grignard reagents, and ene reactions with asymmetric induction levels of 90percent and above.