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- W2950874230 abstract "Because of the high reactivity of Grignard reagents, a direct, highly enantioselective Grignard reaction with aldehydes has rarely been disclosed. In this report, Grignard reagents were introduced with bis[2-(N,N′-dimethylamino)ethyl] ether (BDMAEE) to effectively deactivate their reactivity; thus, a highly enantioselective alkylation of aldehydes with Grignard reagents resulted from catalysis by (S)-BINOL-Ti(OiPr)2. It is thought that BDMAEE chelates the in situ generated salts MgBr2 from a Schlenk equilibrium of RMgBr and Mg(OiPr)Br from transmetalation of RMgBr with Ti(OiPr)4. The Mg salts can actively promote the undesired background reaction to give the racemate. The chelation definitely inhibits the catalytic activity of the Mg salts, suppresses the unwanted background reaction, and enables the highly enantioselective addition catalyzed by (S)-BINOL-Ti(OiPr)2. Consequently, the Mg salt byproducts were not removed, less Ti(OiPr)4 than RMgBr was used, and extremely low temperature was avoided in this ..." @default.
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- W2950874230 date "2011-01-13" @default.
- W2950874230 modified "2023-10-14" @default.
- W2950874230 title "ChemInform Abstract: Catalytic Highly Enantioselective Alkylation of Aldehydes with Deactivated Grignard Reagents and Synthesis of Bioactive Intermediate Secondary Arylpropanols." @default.
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- W2950874230 doi "https://doi.org/10.1002/chin.201106046" @default.
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