Journal
CHEMICAL COMMUNICATIONS
Volume 47, Issue 28, Pages 7917-7932Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1cc10528k
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Funding
- Deutsche Forschungsgemeinschaft [Oe 249/3-2]
- Fonds der Chemischen Industrie
- NRW Graduate School of Chemistry
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The direct enantioselective 1,4-addition of water to alpha,beta-unsaturated acceptors is an open challenge in asymmetric catalysis. Enantioselective conjugate addition of either silicon or boron nucleophiles and subsequent enantiospecific oxidative degradation of the carbon-element bond represents, however, an attractive detour. A single extra step thereby enables an indirect enantiocontrolled construction of (in a broader sense) aldols from alpha,beta-unsaturated carbonyl and carboxyl compounds. While that strategy had been obvious for a long time, it was recent stunning progress in transition metal-catalysed activation of interelement linkages that brought about the solution to that long-standing problem. A concise introduction of existing protocols for stereoselective 1,4-addition of oxygen nucleophiles is followed by a comprehensive summary of the recent rapid advances in transition metal-catalysed (and metal-free) asymmetric conjugate transfer of nucleophilic silicon and boron onto alpha,beta-unsaturated acceptors.
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