Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

被引：5

作者：

Man, Ningning ^{[1
]}

Li, Yuming ^{[1
]}

Jie, Jiyang ^{[1
]}

Li, Hongyun ^{[1
]}

Yang, Haijun ^{[1
]}

Zhao, Yufen ^{[1
]}

Fu, Hua ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 50期

基金：

中国国家自然科学基金;

关键词：

asymmetric synthesis; chiral phosphoric acid; chiral propargylamines; chiral dihydronaphtho[2; 1-b]furans; naphtho[2; ONE-POT SYNTHESIS; ASYMMETRIC MANNICH REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DIRECT-ADDITION; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; CATALYZED REACTION; CASCADE SYNTHESIS; TERMINAL ALKYNES; AMINO ESTERS;

D O I：

10.1002/chem.202102040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N '-di-(tert-butoxycarbonyl)-aminals with beta-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of beta-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

引用

页码：12884 / 12889

页数：6

共 50 条

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