66212-46-2

Upstream product

• 109977-81-3 l-menthyl 3-butenoate 
• 2216-51-5 (-)-menthol 
• 3724-65-0 2-butenoic acid 
• 109977-84-6 d-menthyl 3-butenoate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 625-35-4 trans-chrotonyl chloride 
• 107-93-7 (E)-but-2-enoic acid 

Downstream Products

• 64806-37-7 l-Menthyl β-N-benzylaminobutyrat 
• 79909-51-6 3-(2,2-Dimethoxy-ethyl)-5-methyl-4,5-dihydro-isoxazole-4-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 109977-80-2 (-)-menthyl (E)-4-bromobut-2-enoate 
• 79952-67-3 trans-4-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-5-methylisoxazoline 
• 81076-48-4 cis-4-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-5-methylisoxazoline 
• 81076-39-3 cis-4-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-5-methylisoxazoline 
• 79909-51-6 trans-4-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-5-methylisoxazoline 
• 81038-19-9 trans-5-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-4-methylisoxazoline 
• 81076-49-5 trans-5-menthyloxycarbonyl-3-(2,2-dimethoxyethyl)-4-methylisoxazoline 

Relevant academic research and scientific papers

Application of chiral ligands: Carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters

Chiral Lewis acid mediated 1,3-dipolar cycloaddition reactions of 4-trifluoromethylbenzonitrile oxide to methyl crotonate as well to β-substituted acrylates and (Z)-pent-2-en-1-yl esters were examined. Excellent enantioselectivities with moderate to good regioselectivities were achieved for crotonates with complexes of BiBr3 with (+)-(4,6-benzylidene)methyl-α-d-glucopyranoside C, with the l-ascorbic acid I-FeCl3 system, and with lipase Candida antarctica. High enantiomeric excess was observed for isopropyl ester and benzyl ester. The outstanding ee values were achieved for acrylates with β-t-butyl, cyclohexyl, and 1,3-benzodioxol-5-yl groups in cycloadditions catalyzed by C-Yb(OTf)3 and the (+)-2-hydroxy-3-pinanone N-TiCl4 system. High enantioselectivities were found in reactions of (Z)-pent-2-en-1-yl esters mediated by complexes N-Mg(OTf)2 and N-TiCl4.

Reaction of Chiral Lithium Diorganocopper Reagents, LiRR*Cu, with α,β-Unsaturated Esters of Chiral Alcohols

Conjugate addition of organometallic reagents to chiral esters of trans-3-phenyl-2-propenoic or trans-2-butenoic acid has been studied.The reagents were PhMgBr, LiPh2Cu, LiMe2Cu, LiMeR*Cu, and LiPhR*Cu.The chiral ligand R* was the 2-(1-dimethylaminoethyl)phenyl group.The assymmetric induction varied between 0.3 and 49percent and was in some cases improved by the presence of the R* ligand.The influence of substituents on the β-carbon of the α,β-unsaturated esters on the stereochemical course of the reaction is related to their coordination ability.The directing effects of the chiral ester functions are discussed.