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HFIP solvent enables alcohols to act as alkylating agents in stereoselective heterocyclization

DOI: 10.1021/jacs.9b02198 DOI Help

Authors: Yuxiang Zhu (University of Oxford) , Ignacio Colomer (University of Oxford) , Amber Thompson (University of Oxford) , Timothy J. Donohoe (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Journal Of The American Chemical Society

State: Published (Approved)
Published: April 2019
Diamond Proposal Number(s): 13639

Abstract: 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.

Journal Keywords: Functionalization; Hydrocarbons; Alcohols; Cyclization; Allyl group

Subject Areas: Chemistry, Technique Development

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 15/04/2019 09:27

Discipline Tags:

Organic Chemistry Technique Development - Chemistry Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)