Component-Selective and Stereocontrolled One-Step Three-Component Reaction among Aldehydes, Amines, and Allenyl Boronic Acids or Allenyl Pinacolboronates
Component-Selective and Stereocontrolled One-Step Three-Component Reaction among Aldehydes, Amines, and Allenyl Boronic Acids or Allenyl Pinacolboronates
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DOI：
10.1021/acs.orglett.5b00024
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发表时间：
2015-04-03
期刊：
影响因子：
5.2
通讯作者：
Petasis, Nicos A.
中科院分区：
文献类型：
--
作者：
Liepouri, Fotini;Bernasconi, Giovanni;Petasis, Nicos A.
A one-step, three-component condensation of allenyl boronic acids or allenyl pinacolboronates with amines and aldehydes affords alpha-allenyl or alpha-propargyl alpha-amino acids and anti-beta-amino alcohols. This process gives the allenyl or propargyl product depending on the amine and boron components. Secondary amines generate exclusively alpha-allenyl alpha-amino acids, while primary aliphatic amines lead to alpha-propargyl alpha-amino acids. Secondary aliphatic amines react with chiral alpha-hydroxy aldehydes and allenyl boron derivatives to form stereoselectively allenyl anti-beta-amino alcohol products.
