18930-19-3

Upstream product

• 865444-41-3 (E) and (Z)-4-cyclohexyl-3-buten-1-ol 
• 14886-54-5 methyl 4-oxo-4-cyclohexylbutanoate 
• 15971-95-6 4-cyclohexyl-4-oxo-butyric acid 
• 931-51-1 cyclohexylmagnesiumchloride 
• 1443358-51-7 6-cyclohexyl-2,2-diphenyl-1,2-oxasilinane 
• 2146-67-0 (dichloromethyl)lithium 
• 112630-63-4 2-Cyclohexyl-[1,2]oxaborolane 

Downstream Products

• 18930-20-6 2-cyclohexyltetrahydrofuran 

Relevant academic research and scientific papers

REACTIONS OF 2-ALKYL-, 2-PHENYL- AND 2-ALKOXY-1,2-OXABOROLANES WITH (DICHLOROMETHYL)LITHIUM. A NOVEL SYNTHESIS OF 1,4-ALKANEDIOLS.

Two novel alternative procedures for the synthesis of 1,4-alkanediols were described by involving the reactions of (dichloromethyl)lithium with some 1,2-oxaborolane derivatives readily obtainable from allyl alcohol.

Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans

O-heterocycles bearing tetrasubstituted stereogenic centers are prepared via catalytic chemo- and enantioselective nucleophilic additions to ketoaldehydes, in which the ketone reacts preferentially over the aldehyde. Five- and six-membered rings with both aromatic and aliphatic substituents, as well as an alkynyl substituent, are obtained. Moreover, 2,2,5-trisubstituted and 2,2,5,5-tetrasubstituted tetrahydrofurans are synthesized with excellent stereoselectivities. Additionally, the synthetic utility of the described method is demonstrated with a three-step synthesis of the side chain of anhydroharringtonine.

Ligand-controlled, norbornene-mediated, regio- and diastereoselective rhodium-catalyzed intramolecular alkene hydrosilylation reactions

Ligand-controlled, norbornene-mediated, regio- and diastereoselective rhodium-catalyzed intramolecular alkene hydrosilylation of homoallyl silyl ethers (1) exploiting either BINAP or 1,6-bis(diphenylphosphino)hexane (dpph) has been developed. This method

Gold-catalysed cyclic ether formation from diols

Gold(I) and (III) salts have been found to be highly effective at the catalysis of ether formation from alcohols. Intramolecular ether formation of a 1,5-diol was also achieved, with a stereoselectivity that indicates that an SN1 mechanism predominates. In an attempt to form a seven-membered ring, a stable 14-membered dimer product was also formed. Attempts to control the diastereoselectivity of the reaction using a chiral anionic counterion did not give products with a high de.

Oxygen-directed intramolecular hydroboration

Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S·BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity. Copyright

Regioselective nucleophilic ring opening of epoxides and aziridines derived from homoallylic alcohols

The regioselectivity of nuclcopbilic ring opening of some 3,4-epoxy and 3,4-aziridino alcohols has been studied. The nucleophiles chosen were complex hydrides (LiAlH4, Red-Al and DIBAL) and Lipshutz- or Gilman-type organocuprate reagents. The C-4 substituent in the substrates was varied in order to study steric and electronic effects on the ring opening reactions. For alkyl substituents at C-4, most of the results can be explained on the basis of intramolecular delivery of the nucleophile to C-3 via a six-membered transition state, leading to 1,4-diols or 1,4-amine alcohol derivatives. In general, the epoxy alcohols gave poorer regioselectivity than the N-tosyl aziridino alcohols, for which selectivities of >95:5 were routinely obtained. The activating effect of a phenyl group at C-4 led to a switch in regiochemistry, with the 1,3-diol or 1,3-amino alcohol derivative as the major product.