Alpha-amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for alpha,omega-amino alcohols

Ling He; Jing Yu; Ji Zhang; Xiao-Qi Yu

doi:10.1021/ol070537i

Alpha-amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for alpha,omega-amino alcohols

Org Lett. 2007 Jun 7;9(12):2277-80. doi: 10.1021/ol070537i. Epub 2007 May 11.

Authors

Ling He¹, Jing Yu, Ji Zhang, Xiao-Qi Yu

Affiliation

¹ Department of Chemistry, Key Laboratory of Green Chemistry and Technology, Ministry of Education, Sichuan University, Chengdu, People's Republic of China.

PMID: 17497794
DOI: 10.1021/ol070537i

Abstract

Copper(II) trifluoromethanesulfonate catalyzed the amidation of cyclic ethers with iminoiodanes under mild conditions (CH2Cl2, 40 degrees C) with good yields (up to 86% based on 97% conversion) and selectivity (only alpha-amino products were found). Subsequently, the tosylamidated products could undergo a reductive ring-opening reaction to give alpha,omega-amino alcohols.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Amino Alcohols / chemical synthesis*
Amino Alcohols / chemistry
Catalysis
Ethers, Cyclic / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Amides
Amino Alcohols
Ethers, Cyclic
Organometallic Compounds
copper(II) trifluoromethanesulfonate