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Download fileHFIP Solvent Enables Alcohols To Act as Alkylating Agents in Stereoselective Heterocyclization
journal contribution
posted on 2019-04-12, 10:45 authored by Yuxiang Zhu, Ignacio Colomer, Amber L. Thompson, Timothy J. DonohoeA 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.
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benzyl alcoholscyclization reactionStereoselective Heterocyclizationstereoselective synthesisHFIP Solvent Enables AlcoholsAlkylating Agentsfunctionalized oxygen heterocyclesmethodstoichiometric byproducthomoallylic alcohol substratestereoselective functionalizationalcohol initiatoralkylating agentsSubstoichiometric amountsheterocyclic structuressubstitution pattern
