根据“新和成《中国化学》创新奖”(NHU-CJC Innovation Award)评奖规则，经全体评奖委员会委员投票评选，论文“A Stepwise Annulation for the Transformation of Cyclic Ketones to Fused 6 and 7-Membered Cyclic Enimines and Enones” (DOI: 10.1002/cjoc.201900035)荣获“新和成《中国化学》创新奖”，已在《中国化学》2019年第4期Breaking Reports栏目发表(https://onlinelibrary.wiley.com/doi/10.1002/cjoc.201900035)。

A Stepwise Annulation for the Transformation of Cyclic Ketones to Fused 6 and 7-Membered Cyclic Enimines and Enones

Dong-Ping Wu, Qian He, Dong-Huang Chen, Jian-Liang Ye, and Pei-Qiang Huang*

ABSTRACT  The efficient construction of functionalized polycyclic structures is an important objective in organic synthesis. Herein, we disclose a three-step “[2+n]” annulation method for the transformation of cyclic ketones to fused enimines and enones. The meth­od relies on the Suzuki coupling reaction and the amide reductive alkenylation reaction. A series of fused bicyclic (6/6, 6/7, 8/7) and tricyclic (6/6/6; 6/6/7, 6/5/7) ring systems bearing an á,â-enimine or an á,â-enone functionality have been synthetized in good overall yields.  

KEYWORDS  annulation, ketones, enones, Suzuki coupling, amides

在《中国化学》第四期，我们刊登了福建省化学生物学重点实验室黄培强课题组的一个新工作。该文报道一种从环酮和末端烯烃-酰胺出发经三步以“[2+n]”的方式构建官能化并合碳环的方法。该法以Suzuki偶联和黄培强课题组发展的酰胺还原烯基化反应为关键反应，可方便地构建含á,â-不饱和亚胺或á,â-不饱和烯酮的双环(6/6, 6/7, 8/7)和三环(6/6/6, 6/6/7, 6/5/7)体系。高效构筑含七元环的并合碳环体系是该法的一个亮点。多种类型的含七元环并合碳环体系广泛存在于天然产物中。由于该环合方法兼具底物普适性和灵活性，高产率以及反应条件温和等特点，可望成为全合成中十分有价值的工具。

该研究工作的幕后故事请参见文章:

Polycyclic Structure Synthesis via a Three‐step “[2+n]” Annulation

(https://onlinelibrary.wiley.com/doi/10.1002/cjoc.201900110)