6052-63-7Relevant articles and documents
Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines
Zhao, Lei,Meng, Xiao,Zou, Yifeng,Zhao, Junsong,Wang, Lili,Zhang, Lanlan,Wang, Chao
supporting information, p. 8516 - 8521 (2021/10/25)
We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.
Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution
Lee, Yeosan,Park, Jinyoung,Cho, Seung Hwan
supporting information, p. 12930 - 12934 (2018/09/25)
We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the β-position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks.
Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative
Lu, Jia-Tian,Shi, Zi-Fa,Cao, Xiao-Ping
supporting information, p. 7774 - 7782 (2017/08/14)
An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.