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由醛和异氰化物一锅法合成N-取代的β-氨基醇

One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides.

作者信息

Cioc Răzvan C, van der Niet Daan J H, Janssen Elwin, Ruijter Eelco, Orru Romano V A

机构信息

Department of Chemistry & Pharmaceutical Sciences and Amsterdam Institute for Molecules Medicines and Systems (AIMMS), VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam (The Netherlands).

出版信息

Chemistry. 2015 May 18;21(21):7808-13. doi: 10.1002/chem.201500210. Epub 2015 Apr 13.

Abstract

A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.

摘要

已开发出一种实用的两阶段一锅法合成 N-取代β-氨基醇的方法,该方法以醛和异氰化物为起始原料。该方法具有反应条件温和、适用范围广和对官能团普遍耐受性的特点。基于一种不太常见的中心碳-碳键断裂方式,该方案补充了涉及胺和各种碳亲电试剂(环氧化物、α-卤代酮、β-卤代醇)的传统方法。如抗哮喘药物沙丁胺醇的合成所示,可从简单的构建单元以简洁有效的方式制备与药物相关的产品。将该合成升级为对映选择性变体也是可行的。

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