Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate

An Enantioselective Multicomponent Carbonyl Allylation of Aldehydes with Dienes and Alkynyl Bromides Enabled by Chiral Palladium Phosphate
Liu-Zhu Gong, Zhi-Yong Han, Pu-Sheng Wang, Zhong-Lin Tao, Hong-Cheng Shen
An enantioselective multicomponent carbonyl allylation reaction of 1,3-butadienes, alkynyl bromides and aldehydes has been established, leading to the generation of densely functionalized homoallylic alcohols in high levels of structural diversity and stereoselectivity. The multicomponent process sequentially comprises the oxidative addition, salt metathesis, insertion/π-allyl-Pd formation, asymmetric allylic borylation, and enantioslecitve carbonyl allylborylation, wherein the alkynyl palladium phosphate in situ generated from the chiral silver phosphate and the alkynyl palladium bromide turns out to be a key intermediate that allows the efficient stereochemical control.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700621

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