Literature DB >> 29741877

Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process.

Keiji Mori1, Ryo Isogai2, Yuto Kamei3, Masahiro Yamanaka3, Takahiko Akiyama2.   

Abstract

Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp3)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1,5]-hydride shift).

Entities:  

Year:  2018        PMID： 29741877     DOI： 10.1021/jacs.8b02761

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


  15 in total

1.  Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors:  Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2020-01-27       Impact factor: 6.005

2.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

Authors:  Yernaidu Reddi; Cheng-Che Tsai; Carolina M Avila; F Dean Toste; Raghavan B Sunoj
Journal:  J Am Chem Soc       Date:  2018-12-28       Impact factor: 15.419

3.  α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors:  Anirudra Paul; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

4.  Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors:  Anirudra Paul; Alafate Adili; Daniel Seidel
Journal:  Org Lett       Date:  2019-03-06       Impact factor: 6.005

5.  Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors:  Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal:  Org Lett       Date:  2018-06-25       Impact factor: 6.005

6.  Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)-H bond functionalization.

Authors:  Keiji Mori; Nobuaki Umehara; Takahiko Akiyama
Journal:  Chem Sci       Date:  2018-06-25       Impact factor: 9.825

7.  Redox-triggered cascade dearomative cyclizations enabled by hexafluoroisopropanol.

Authors:  Shuai-Shuai Li; Xintong Lv; Didi Ren; Chang-Lun Shao; Qing Liu; Jian Xiao
Journal:  Chem Sci       Date:  2018-09-13       Impact factor: 9.825

8.  Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Authors:  Anirudra Paul; Jae Hyun Kim; Scott D Daniel; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-17       Impact factor: 15.336

9.  Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.

Authors:  Yang Zheng; Ping Dai; Dafang Gao; Kemiao Hong; Luyao Kou; Shanliang Dong; Jundie Hu; Lihua Qiu; Wenhao Hu; Xiaoguang Bao; Xinfang Xu
Journal:  iScience       Date:  2020-05-15

10.  Chemo- and Regioselective Synthesis of Acyl-Cyclohexenes by a Tandem Acceptorless Dehydrogenation-[1,5]-Hydride Shift Cascade.

Authors:  Lewis B Smith; Roly J Armstrong; Daniel Matheau-Raven; Timothy J Donohoe
Journal:  J Am Chem Soc       Date:  2020-01-22       Impact factor: 15.419
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