Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
Org Lett. 2023 Mar 31;25(12):2068-2072. doi: 10.1021/acs.orglett.3c00425. Epub 2023 Mar 20.
The organocatalytic asymmetric reactions of C2-unsubstituted racemic naphthyl-indoles with orthoalkynylnaphthols were employed to synthesize axially chiral styrenes connected to an axially chiral naphthyl-indole unit. Utilizing chiral phosphoric acid as the catalyst, these axially chiral styrenes were prepared in good yields (up to 96%) and excellent stereoselectivity (up to >99.9% ee, >20:1 dr, and >99:1 /) in mild conditions. Moreover, further synthetic transformations were achieved with high yields and excellent stereocontrol.
手性磷酸作为催化剂，在手性膦酸催化的条件下，通过 C2-未取代的外消旋萘基-吲哚与邻炔基萘酚的不对称反应，以温和的条件，高收率（高达 96%）和优异的对映选择性（高达>99.9%ee，>20:1dr，和>99:1/），制备了轴手性苯乙烯连接到轴手性萘基-吲哚单元上。此外，通过进一步的合成转化，实现了高收率和优异的立体控制。
