97235-28-4

Upstream product

• 75-09-2 dichloromethane 
• 97235-26-2 2-(<1S,2S>-trans-2-phenylcyclopentyl)-1,3,2-dioxaboriniane 
• 591-51-5 phenyllithium 
• 123126-64-7 N-(1-cyclopentenylmethylidene)cyclohexylamine 
• 97276-81-8 (1S,2S)-(+)-trans-2-phenylcyclopentanecarboxaldehyde 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 108-98-5 thiophenol 
• 131140-05-1 (1'R,2'R)-2'-Hydroxycyclohexyl (E)-6-chloro-2-hexenoate 
• 107408-77-5 (E)-6-chloro-2-hexenoyl chloride 
• 131233-20-0 (1S,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate 

Relevant academic research and scientific papers

Chiral alcohol-induced diastereoselective conjugate addition and cyclization

Conjugate addition of organocuprate reagents to α,β-unsaturated esters of chiral trans-cyclohexanediol proceeded diastereoselectively, and the intramolecular trapping of the generated enolate also afforded asymmetric cyclization products.

Chiral Synthesis via Organoboranes. 4. Synthetic Utility of Boronic Esters of Essentially 100percent Optical Purity. Synthesis of Homologated Boronic Acids and Esters of Very High Enantiomeric Purities

2-Alkyl-1,3,2-dioxaborinanes, R*BO2(CH2)3, of essentially 100percent optical purity, prepared by the asymmetric hydroboration of readily available prochiral olefins with subsequent removal of the chiral auxiliary, can be homologated to α-chloroalkyl derivatives, R*CHClBO2(CH2)3, of essentially 100percent ee by reaction with LiCHCl2.The intermediates R*CHClBO2(CH2)3 are smoothly reduced with KIPBH to give the corresponding one-carbon-homologated boronic esters R*CH2BO2(CH2)3 in very high optical purity.The operation can be repeated to produce R*CH2CH2BO2(CH2)3 etc.Consequently, it is now possible to synthesize a wide variety of optically active boronic esters, not available by direct asymmetric hydroboration, either (+) or (-), in essentially 100percent ee, and to convert these into synthetically valuable compounds.