通过远程活化实现膦催化的γ-取代肉桂醛衍生的森田-贝利斯-希尔曼碳酸酯的(3 + 2)环化反应
Phosphine-Catalyzed (3 + 2) Annulation of γ-Substituted Cinnamic Aldehyde-Derived Morita-Baylis-Hillman Carbonates through Remote Activation.
作者信息
Ren Yue, Shi Wangyu, Tang Yi, Piao Shixiang, Yu Songcheng, Wu Yongjun, Guo Hongchao
机构信息
Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, P. R. China.
College of Public Health, Zhengzhou University, Zhengzhou 450001, P. R. China.
出版信息
Org Lett. 2023 Oct 13;25(40):7374-7379. doi: 10.1021/acs.orglett.3c02887. Epub 2023 Oct 2.
A series of γ-substituted Morita-Baylis-Hillman (MBH) carbonates were synthesized and subjected to phosphine-catalyzed annulations with electrophilic exocyclic alkenes, giving various valuable spirocyclopentenes in moderate to excellent yields with moderate to excellent diastereoselectivities. A large scope of MBH carbonates bearing γ-hydrogen, alkenyl, and alkynyl substituents was well tolerated. The annulation unprecedentedly involves β-, γ-, and δ-carbons of MBH carbonates.
合成了一系列γ-取代的Morita-Baylis-Hillman（MBH）碳酸酯，并使其与亲电外环烯烃进行膦催化环化反应，以中等至优异的产率和中等至优异的非对映选择性得到了各种有价值的螺环戊烯。带有γ-氢、烯基和炔基取代基的多种MBH碳酸酯都具有良好的耐受性。该环化反应前所未有的涉及到MBH碳酸酯的β-、γ-和δ-碳。
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