193468-09-6

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 583-60-8 2-Methylcyclohexanone 

Downstream Products

• 161151-77-5 *,S^*)>-α-(acetyloxy)-1-methyl-2-oxocyclohexanepropanoic acid methyl ester 
• 178613-68-8 (3S,1'R)-3-[(2-oxo-1-methylcyclohexyl)methyl]-2(5H)-3,4-dihydrofuranone 
• 94089-45-9 3-{(R)-1-Methyl-2-[(E)-(S)-1-phenyl-ethylimino]-cyclohexyl}-propionic acid methyl ester 
• 179915-19-6 (E)-3-((R)-1-Methyl-2-oxo-cyclohexyl)-acrylic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Formal Total Synthesis of (-)-Dysidiolide

(matrix presentd) An enantioselective formal total synthesis of the sesterterpene (-)-dysidiolide 1 beginning with an intermolecular Diels-Alder reaction of the allene ester 3 and the silyloxydiene 10 is reported.

Use of α-amino esters as chiral auxiliaries in the enantioselective Michael alkylation of chiral imines

A study concerning the regio- and stereoselectivities of the Michael reaction between chiral imines and electrophilic olefins has been performed with α-amino esters as chiral auxiliaries. In all cases, optically active 1-phenylethylamine, which is usually

Total synthesis and absolute configuration of riccardiphenols A and B, isolated from the Liverwort Riccardia crassa

The title compounds were synthesized as optically active forms using chiral Michael addition of the imine, prepared from 2-methylcyclohexanone and (S)-(-)-phenylethylamine, to methyl propiolate. The etherification of the intermediate triol was accomplished by TsOH-catalyzed cyclization. The absolute configurations of the natural products, riccardiphenols A and B, were established as 1 and 2, respectively.

Diastereoselectivity and Enantioselectivity in the Addition of Chiral Imines of 2-Methylcyclohexanone to Crotonic and Methacrylic Acid Esters

Additions of the chiral imine (reacting as its secondary enamine tautomer) obtained from (S)-1-phenylethylamine and 2-methylcyclohexanone were performed with the phenyl ester of crotonic and methacrylic acid as well as with their methyl ester.In each example, the stereochemical relationship of the substituents in the major adduct was shown to be the one predicted in a previous theoretical calculation which established that the reactants complex has a chairlike geometry.In all the examples, the diastereoselectivity is superior to 98percent.The enantioselectivity of the reactions is excellent as is usually the case with unsubstituted electrophilic olefins, the example with phenyl methacrylate being particularly remarkable (de and ee >99percent).In each case the favored diastereofacial selectivity is again in accordance with the rule elaborated previously.Relevant facts about the influence of the substituents upon the reactivity, the proportion of regioisomers, the stereoselectivity, and the enantioselectivity of the reaction are given.

ASYMMETRIC MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES. ENANTIOSELECTIVE SYNTHESES OF (-)-GEOSMIN AND TWO OTHER RELATED NATURAL TERPENES, AS WELL AS ENANT-(+)-GEOSMIN

Natural (-)-geosmin 11, (+)-octalone 14 (from Vetiveria zizanioides), and (+)-octalin 15 (from Bazzania fauriana and B. angustifolia) have been prepared in high chemical and enantiomeric yields via the asymmetric process involving Michael-type alkylation of chiral imines 6 and 12.Enant-(+)-geosmin has been also synthesized by the same procedure.