Mengting Tan, Yunping Zheng, Sen Zhang, Hui Yao, Xin Yan, Xing Zhao, Mingguo Liu, Nianyu Huang, Nengzhong Wang
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Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates
Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series of cis-2,3-disubstituted indolines and cyclopropane-fused tetrahydroquinolines were obtained via two pathways with a broad substrate scope in moderate to excellent yields under transition-metal-free conditions. It is noteworthy that the γ-bromocrotonates could be used as C1 or C2 synthons by modulating the base; in particular, the γ-bromocrotonates were used as both nucleophiles and electrophiles to generate cyclopropanes for the first time.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.