200731-68-6

Upstream product

• 70982-26-2 (1R,4S)-1,7,7-trimethyl-2-(trimethylsilyloxy)bicyclo[2.2.1]hept-2-en 
• 90-99-3 diphenylchloromethane 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 

Downstream Products

• 479686-18-5 (1S,2S,3R,4S)-3-Benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 372947-58-5 Acetic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-67-6 (E)-3-Phenyl-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-59-6 3-Hydroxy-3-phenyl-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-68-7 (E)-3-(2-Methoxy-phenyl)-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-71-2 (E)-3-(4-Fluoro-phenyl)-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-70-1 (E)-3-(4-Methoxy-phenyl)-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-69-8 (E)-3-(3-Methoxy-phenyl)-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-63-2 3-(4-Fluoro-phenyl)-3-hydroxy-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-60-9 3-Hydroxy-3-(2-methoxy-phenyl)-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-62-1 3-Hydroxy-3-(4-methoxy-phenyl)-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-61-0 3-Hydroxy-3-(3-methoxy-phenyl)-propionic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-72-3 (E)-3-Naphthalen-2-yl-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 372947-74-5 (E)-3-Benzo[1,3]dioxol-5-yl-acrylic acid (1R,2R,3S,4R)-3-benzhydryl-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers

The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58-90% de). In all cases, small amounts (2-symmetric dl-3,4-diaryladipic acids and trans-3,4-diarylcyclopentanones. The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, prepared from (1R)-(+)-camphor, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.

Stereoselective hydrocoupling of [(1R)-exo]-3-exo-(diphenylmethyl)bornyl cinnamates by electroreduction

Equation presented The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, synthesized from (1R)-(+)-camphor in three steps, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrod

Asymmetric Conversion of Arenechromium Complexes to Functionalized Cyclohexenones: Progress toward Defining an Optimum Chiral Auxiliary

An investigation into the asymmetric synthesis of 5-substituted cyclohexenones via nucleophile addition to (alkoxyarene)chromium tricarbonyl complexes is described. Diastereoselectivity during the nucleophile addition step was achieved using alkoxy substituents derived from terpenoid substrates as chiral auxiliaries. Selectivities as high as 24:1 were obtained when 2-phenylisoborneol was used as the chiral auxiliary and as high as 17:1 using 3,3-(ethylenedioxy)isoborneol. The absolute stereochemistry of the major products was assigned by Mosher's method, after their conversion to the corresponding cyclohexenol. A study of the temperature dependence of the nucleophile addition to alkoxytoluene complexes revealed a thermodynamic preference for addition ortho to the ether substituent.