Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles.

作者: Eduard Hartmann , Devendra J. Vyas , Martin Oestreich

DOI: 10.1039/C1CC10528K

关键词: NucleophileConjugateChemistryStereoselectivityCombinatorial chemistryOrganic chemistryEnantioselective synthesisSiliconOxidative degradationBoron

摘要: The direct enantioselective 1,4-addition of water to α,β-unsaturated acceptors is an open challenge in asymmetric catalysis. Enantioselective conjugate addition either silicon or boron nucleophiles and subsequent enantiospecific oxidative degradation the carbon–element bond represents, however, attractive detour. A single extra step thereby enables indirect enantiocontrolled construction (in a broader sense) aldols from carbonyl carboxyl compounds. While that strategy had been obvious for long time, it was recent stunning progress transition metal-catalysed activation interelement linkages brought about solution long-standing problem. concise introduction existing protocols stereoselective oxygen followed by comprehensive summary rapid advances (and metal-free) transfer nucleophilic onto acceptors.

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