40596-14-3Relevant articles and documents
HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization
Zhu, Yuxiang,Colomer, Ignacio,Thompson, Amber L.,Donohoe, Timothy J.
, p. 6489 - 6493 (2019/05/06)
A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.
Iridium-Catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hydroacylation products
Hatanaka, Shintaro,Obora, Yasushi,Ishii, Yasutaka
experimental part, p. 1883 - 1888 (2010/06/20)
A novel iridium-catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2-alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β- unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ-unsatutated ketones and then isomerisation, which leads to the hydroacylation products.
Reductive cleavage of 2-methyleneoxetanes with lithium and 4,4'-di-tert- butylbiphenyl
Hashemzadeh, Mehrnoosh,Howell, Amy R.
, p. 1855 - 1858 (2007/10/03)
3,3-Dimethyl-2-mcthylene-4-phenyloxetane (5) undergoes reductive cleavage with lithium and 4,4'-di-tertbutylbiphenyl (DTBB) to give an intermediate dianion, which reacts regioselectively with aldehydes and ketones to give aldol adducts in modest yields. A
