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Synfacts 2017; 13(10): 1063
DOI: 10.1055/s-0036-1591258
DOI: 10.1055/s-0036-1591258
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Synthesis of Chiral Homoallylic Alcohols by a Palladium-Catalyzed Cascade Reaction
Shen H.-C.
Wang P.-S.
Tao Z.-L.
Han Z.-Y.
Gong L.-Z.
* University of Science and Technology of China, Hefei, P. R. of China
An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate.
Adv. Synth. Catal. 2017;
359: 2383-2389
An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate.
Adv. Synth. Catal. 2017;
359: 2383-2389
Further Information
Publication History
Publication Date:
18 September 2017 (online)
Significance
The authors disclose a highly selective synthesis of homoallylic alcohols featuring a cascade insertion–carbopalladation–borylation–allylation sequence. Products of this type can be used as building blocks for natural products or pharmaceutical compounds.
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Comment
The high stereoselectivity arises from an enantioselective borylation and a boron-mediated allylation, in which one transition state is disfavored due to gauche interactions. These interactions account for the extremely high Z/E selectivity.
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