Synthesis of 2H-Chromenes via Hydrazine-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis

被引：39

作者：

Zhang, Yunfei ^{[1
]}

Jermaks, Janis ^{[1
]}

MacMillan, Samantha N. ^{[1
]}

Lambert, Tristan H. ^{[1
]}

机构：

[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

ACS CATALYSIS | 2019年 / 9卷 / 10期

基金：

美国国家卫生研究院;

关键词：

Carbonyl-olefin metathesis; hydrazines; chromenes; cycloaddition; cycloreversion; DERIVATIVES;

D O I：

10.1021/acscatal.9b03656

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The catalytic ring-closing carbonyl-olefin metathesis (RCCOM) of O-allyl salicylaldehydes to form 2H-chromenes is described. The method utilizes a [2.2.1]-bicyclic hydrazine catalyst and operates via a [3 + 2]/retro-[3 + 2] metathesis manifold. The nature of the allyl substitution pattern was found to be crucial, with sterically demanding groups such as adamantylidene or diethylidene offering optimal outcomes. A survey of substrate scope is shown along with a discussion of mechanism supported by DFT calculations. Steric pressure arising from syn-pentane minimization of the diethylidene moiety is proposed to facilitate cycloreversion.

引用

页码：9259 / 9264

页数：11

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