Jiang Fei, Luo Gui-Zhen, Zhu Zi-Qi, Wang Cong-Shuai, Mei Guang-Jian, Shi Feng
School of Chemistry and Materials Science , Jiangsu Normal University , Xuzhou , 221116 , China.
J Org Chem. 2018 Sep 7;83(17):10060-10069. doi: 10.1021/acs.joc.8b01390. Epub 2018 Aug 23.
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.
已利用萘基吲哚衍生的膦（NIP）作为有机催化剂，实现了邻醌甲基化物（o-QMs）与MBH碳酸酯的有机催化[4 + 1]环化反应。通过这种方法，一系列2,3-二氢苯并呋喃衍生物得以高产率和优异的非对映选择性（产率高达99%，非对映体比例>95:5）合成出来。该反应不仅实现了首例邻醌甲基化物与MBH碳酸酯的[4 + 1]环化反应，还代表了萘基吲哚衍生的膦作为有机催化剂在催化反应中的首次应用。此外，该反应还为构建2,3-二氢苯并呋喃骨架提供了一种有用的方法。
