Application of Naphthylindole-Derived Phosphines as Organocatalysts in [4+1] Cyclizations of o-Quinone Methides with Morita-Baylis-Hillman Carbonates

被引：62

作者：

Jiang, Fei ^{[1
]}

Luo, Gui-Zhen ^{[1
]}

Zhu, Zi-Qi ^{[1
]}

Wang, Cong-Shuai ^{[1
]}

Mei, Guang-Jian ^{[1
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 17期

基金：

中国国家自然科学基金;

关键词：

IN-SITU; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; HYDROXYBENZYL ALCOHOLS; ACTIVATION STRATEGY; FACILE SYNTHESIS; CYCLOADDITION; ACID; ANNULATION; CATALYSIS;

D O I：

10.1021/acs.joc.8b01390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic [4 + 1] cyclization of o-QMs with MBH carbonates has been established using naphthylindole-derived phosphine (NIP) as an organocatalyst. By using this approach, a series of 2,3-dihydrobenzofuran derivatives have been synthesized in high yields and excellent diastereoselectivities (up to 99% yield, >95:5 dr). This reaction not only has established the first [4 + 1] cyclization of o-QMs with MBH carbonates but also represents the first application of naphthylindole-derived phosphines as organocatalysts in catalytic reactions. In addition, this reaction has also provided a useful method for constructing 2,3-dihydrobenzofuran scaffolds.

引用

页码：10060 / 10069

页数：10

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