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• W1924146957 endingPage "755" @default.
• W1924146957 startingPage "748" @default.
• W1924146957 abstract "We have demonstrated a highly diastereoselective synthesis of optically pure Ar-BINMOL-derived diols and their analogues. The present study demonstrates a unique cascade chirality transfer in a [1,2]-Wittig rearrangement that leads to chiral diols with three stereogenic centers, which include a chiral sp3 center at the alcohol and C2-axial chirality. Screening these ligands in the arylation of aromatic aldehydes with Grignard reagents shows that the naphthyl-substituted BINMOL promotes the aryl transfer reaction in good yields (70–92 %) and moderate-to-good enantioselectivities (up to 72 % ee), and a series of control experiments substantiates that the axial chirality and the chiral sp3 center at the alcohol of the Ar-BINMOLs are the pivotal enantioselectivity-controlling structure elements. In addition, this study demonstrated the importance of the chiral sp3 center at the alcohol on Ar-BINMOL for the aryl transfer reaction. Finally, we found that the chiral Ar-BINMOL ligand 2h mediated the titanium-promoted 1,2-addition of MeMgBr to aldehydes to give the desired products in good yields with excellent enantioselectivities (up to 92 % ee)." @default.
• W1924146957 created "2016-06-24" @default.
• W1924146957 creator A5019478505 @default.
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• W1924146957 creator A5046927622 @default.
• W1924146957 creator A5064893364 @default.
• W1924146957 creator A5076542174 @default.
• W1924146957 date "2012-12-05" @default.
• W1924146957 modified "2023-10-16" @default.
• W1924146957 title "Synthesis of Ar-BINMOL Ligands by [1,2]-Wittig Rearrangement to Probe Their Catalytic Activity in 1,2-Addition Reactions of Aldehydes with Grignard Reagents" @default.
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• W1924146957 doi "https://doi.org/10.1002/ejoc.201201301" @default.
• W1924146957 hasPublicationYear "2012" @default.
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