Literature DB >> 22394013

Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines.

Takahiro Nishimura1, Akira Noishiki, Gavin Chit Tsui, Tamio Hayashi.   

Abstract

Asymmetric addition of arylboroxines to cyclic N-sulfonyl ketimines proceeded in the presence of a rhodium catalyst coordinated with a chiral diene ligand to give high yields of benzosultams, where a triaryl-substituted stereogenic carbon center was created with high enantioselectivity (93-99% ee). The chiral benzosultams were transformed into the chiral (triaryl)methylamines by breaking the cyclic structure.

Entities:  

Year:  2012        PMID: 22394013     DOI: 10.1021/ja300697c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Jixin Liu; Clarissa A Shoffler; Glenn P A Yap; Mary P Watson
Journal:  Org Lett       Date:  2016-11-16       Impact factor: 6.005

2.  Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols.

Authors:  Guangfan Zheng; Yan Li; Jingjie Han; Tao Xiong; Qian Zhang
Journal:  Nat Commun       Date:  2015-04-22       Impact factor: 14.919

3.  Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines.

Authors:  Jiawei Rong; Juan F Collados; Pablo Ortiz; Ravindra P Jumde; Edwin Otten; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2016-12-23       Impact factor: 14.919

4.  Ni(II)-catalyzed asymmetric alkenylations of ketimines.

Authors:  Mao Quan; Xiaoxiao Wang; Liang Wu; Ilya D Gridnev; Guoqiang Yang; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919

5.  Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Sulfamidate Imines: Efficient Synthesis of Chiral Cyclic Sulfamidates.

Authors:  Yuanhua Liu; Zhiyuan Yi; Xuefeng Tan; Xiu-Qin Dong; Xumu Zhang
Journal:  iScience       Date:  2019-07-04

6.  Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

Authors:  Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin
Journal:  iScience       Date:  2019-10-30

7.  Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

Authors:  Charlotte A Osborne; Thomas B D Endean; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2015-10-27       Impact factor: 6.005

8.  Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Michael Callingham; Benjamin M Partridge; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-11-24       Impact factor: 15.336

9.  The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions.

Authors:  Takahiro Sawano; Pengfei Ji; Alexandra R McIsaac; Zekai Lin; Carter W Abney; Wenbin Lin
Journal:  Chem Sci       Date:  2015-09-14       Impact factor: 9.825

Review 10.  Recent Advances in Catalytic Synthesis of Benzosultams.

Authors:  Quan-Qing Zhao; Xiao-Qiang Hu
Journal:  Molecules       Date:  2020-09-23       Impact factor: 4.411

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