Component-Selective and Stereocontrolled One-Step Three-Component Reaction among Aldehydes, Amines, and Allenyl Boronic Acids or Allenyl Pinacolboronates

被引：40
作者：
Liepouri, Fotini
Bernasconi, Giovanni
Petasis, Nicos A. [1 ]
机构：
[1] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 07期
基金：
美国国家卫生研究院;
关键词：
CARBON BOND FORMATION; ORGANOBORONIC ACIDS; PRACTICAL REAGENT; PETASIS REACTION; ALCOHOLS; ESTERS; SALICYLALDEHYDES; EFFICIENT; IMINES;
D O I：
10.1021/acs.orglett.5b00024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1628 / 1631
页数：4
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