172288-96-9

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 1169707-66-7 (R,Z)-1-cyclohexylbut-2-ene-1,4-diol 
• 446246-14-6 (1R,2S,6R,7S)-1,10,10-trimethyl-5-[(1R)-2-oxo-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 
• 446246-10-2 (1R,2S,6R,7S)-5-[(1R,2R)-2-hydroxy-2-cyclohexyl-1-(phenylsulfanyl)ethyl]-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0^2,6]decan-4-one 

Downstream Products

• 59411-58-4 (R)-1-cyclohexylethane-1,2-diol 
• 53585-93-6 (R)-(-)-hexahydromandelic acid 

Relevant academic research and scientific papers

Asymmetric 1,4-dihydroxylation of 1,3-dienes by catalytic enantioselective diboration

(Chemical Equation Presented) Asymmetric 1,4-dihydroxylations of 1,3-dienes, and other transformations, are initiated by the Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B2(pin) 2) to conjugated dienes. The studies reported in this communication suggest that both cyclic and acyclic substrates will participate in this reaction; however, dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway. In addition to oxidation to the derived 2-buten-1,4-diol, stereoselective carbonyl allylation with the intermediate bis(boronate) ester is also described.

Lithiated camphor-derived oxazolidinone S,N-acetals as chiral formyl anion synthons in additions to aldehydes. Asymmetric synthesis of α-hydroxy aldehydes and α-hydroxy acids

N-(Phenylthiomethyl)oxazolidinones derived from camphor can be lithiated and added to aldehydes in good yields and stereoselectivities. The adducts are crystalline, which simplifies isolation of the major diastereomer from the product mixture. Hydrolysis affords enantiopure α-hydroxy aldehydes, which can be oxidized to α-hydroxy acids in good yields. The steric course of the reaction is analyzed in detail and a mechanistic model is presented.