6652-28-4Relevant articles and documents
Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones
Wu, Hua,Wang, Qian,Zhu, Jieping
supporting information, p. 5858 - 5861 (2017/05/12)
We report an unprecedented organocatalytic enantioselective acyloin rearrangement of α,α-disubstituted α-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, α-hydroxy acetals rearranged to α-alkoxy ketones in good to high yields with high enantioselectivities. Formation of an ion pair between the in situ generated oxocarbenium ion and the chiral phosphoramide anion was proposed to be responsible for the highly efficient transfer of chirality. Conditions for removal of cyclohexyl and cyclopentyl groups from the corresponding α-alkoxy ketones were uncovered underpinning their potential general utility as hydroxy protecting groups. Conversion of the rearranged products to the enantioenriched α-hydroxy ketone, 1,2-diol, β-amino alcohol and 1,4-dioxane was also documented.
Bisbenzoin ethers and method of producing benzoin ethers
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, (2008/06/13)
New bisbenzoin ethers are produced. The method of producing the bisbenzoin ethers comprises the reaction of an alkyl glycol with benzoin utilizing phosphorous oxychloride as the catalyst with hydrogen chloride as acid reacting agent. The use of phosphorous oxychloride as catalyst with hydrogen chloride improves the production of benzoin ethers in general by the reaction of benzoin with the selected alcohol.