898269-04-0Relevant articles and documents
Rhodium-Catalyzed Asymmetric Addition of Organoboronic Acids to Aldimines Using Chiral Spiro Monophosphite-Olefin Ligands: Method Development and Mechanistic Studies
Shan, Huanyu,Zhou, Qiaoxia,Yu, Jinglu,Zhang, Shuoqing,Hong, Xin,Lin, Xufeng
, p. 11873 - 11885 (2018)
The synthesis of a novel type of chiral spiro monophosphite-olefin (SMPO) ligands based on a hexamethyl-1,1′-spirobiindane scaffold was accomplished starting from Bisphenol C. The optimal ligand could serve as an elegant chiral bidentate ligand in the Rh-catalyzed asymmetric 1,2-addition of organoboronic acids to various acyclic/cyclic aldimines, leading to chiral amines with high yields and excellent enantioselectivities. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations and postulated the origins of the higher enantioselectivity of phosphite-olefin ligands.
Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to: N-tosylarylimines
Xue, Feng,Liu, Qibin,Zhu, Yong,Qing, Yunfei,Wan, Boshun
, p. 25377 - 25381 (2019/08/28)
An efficient Rh-catalyzed addition of arylboronic acids to N-tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective.
Design and synthesis of new chiral phosphorus-olefin bidentate ligands and their use in the rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl imines
Shintani, Ryo,Narui, Rintaro,Tsutsumi, Yosuke,Hayashi, Sayuri,Hayashi, Tamio
supporting information; experimental part, p. 6123 - 6125 (2011/07/30)
Novel chiral phosphorus-olefin bidentate ligands have been synthesized in a few steps from a readily available enantiopure compound. These ligands have been applied to a rhodium-catalyzed asymmetric addition of organoboroxines to N-sulfonyl aldimines, achieving high yield and enantioselectivity.
An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric addition of arylboronic acids to N-sulfonylarylaldimines
Kurihara, Kazunori,Yamamoto, Yasunori,Miyaura, Norio
experimental part, p. 260 - 270 (2009/09/06)
A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) was newly developed for the rhodium-catalyzed enantioselective addition of arylboronic acids to N-sulfonylimines. This ligand achieved high enantioselectivities in a range of
Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids
Duan, Hai-Feng,Jia, Yi-Xia,Wang, Li-Xin,Zhou, Qi-Lin
, p. 2567 - 2569 (2007/10/03)
The asymmetric arylation of N-tosylarylimines with arylboronic acids was realized by using rhodium/(S)-ShiP as catalyst. The reaction proceeded in aqueous toluene to give diarylmethylamines in good yields with up to 96% ee.