区域选择性
对映选择合成
化学
氢胺化
配体(生物化学)
电泳剂
组合化学
试剂
肉桂酸
有机化学
手性配体
立体化学
催化作用
生物化学
受体
作者
Sheng Guo,Jiaqi Zhu,Stephen L. Buchwald
标识
DOI:10.1002/anie.202007005
摘要
Abstract A Cu‐catalyzed enantioselective hydroamination of α,β‐unsaturated carbonyl compounds for the synthesis of β‐amino acid derivatives was achieved through ligand‐controlled reversal of the hydrocupration regioselectivity. While the hydrocupration of α,β‐unsaturated carbonyl compounds to form α‐cuprated species has been extensively investigated, we report herein that, in the presence of an appropriate ancillary chiral ligand, the opposite regiochemistry can be observed for cinnamic acid derivatives, leading to the delivery of the copper to the β‐position. This copper can react with an electrophilic aminating reagent, 1,2‐benzisoxazole, to provide enantioenriched β‐amino acid derivatives, which are important building blocks for the synthesis of natural products and bioactive small molecules.
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