Literature DB >> 34321717

C-H Insertion Reactions of Donor/Donor Carbenes: Inception, Investigation, and Insights.

Jared T Shaw1.   

Abstract

Insertion reactions of donor/donor carbenes have emerged from obscurity to become a versatile method for the synthesis of a variety of cyclic structures with excellent control of diastereo- and enantioselectivity. This Account describes the origin of this project as part of a natural product synthesis and the ensuing decade of reaction development that has resulted in new asymmetric methods as well as intriguing tangential observations.

Entities:  

Keywords:  C–H insertion; asymmetric catalysis; carbenes; rhodium

Year:  2020        PMID： 34321717      PMCID： PMC8315035          DOI： 10.1055/s-0039-1691738

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  14 in total

1.  Synthesis of (-)-viriditoxin: a 6,6'-binaphthopyran-2-one that targets the bacterial cell division protein FtsZ.

Authors:  Young Sam Park; Charles I Grove; Marcos González-López; Sameer Urgaonkar; James C Fettinger; Jared T Shaw
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

2.  Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C-H Insertion of Donor/Donor Carbenes.

Authors:  Lucas W Souza; Richard A Squitieri; Christine A Dimirjian; Blanka M Hodur; Leslie A Nickerson; Corinne N Penrod; Jesus Cordova; James C Fettinger; Jared T Shaw
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-18       Impact factor: 15.336

3.  Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements.

Authors:  Christine A Dimirjian; Marta Castiñeira Reis; Edward I Balmond; Nolan C Turman; Elys P Rodriguez; Michael J Di Maso; James C Fettinger; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2019-09-05       Impact factor: 6.005

4.  Ruthenium porphyrin catalyzed intramolecular carbenoid C[bond]H insertion. Stereoselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles.

Authors:  Wai-Hung Cheung; Shi-Long Zheng; Wing-Yiu Yu; Guo-Chuan Zhou; Chi-Ming Che
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

5.  Synthesis of Esters by in Situ Formation and Trapping of Diazoalkanes.

Authors:  Richard A Squitieri; Galen P Shearn-Nance; Jason E Hein; Jared T Shaw
Journal:  J Org Chem       Date:  2016-06-13       Impact factor: 4.354

6.  Copper- or Thermally Induced Divergent Outcomes: Synthesis of 4-Methyl 2H-Chromenes and Spiro-4H-Pyrazoles.

Authors:  Yang Zheng; Lihua Qiu; Kemiao Hong; Shanliang Dong; Xinfang Xu
Journal:  Chemistry       Date:  2017-11-30       Impact factor: 5.236

7.  Antibacterial activity of flavanostilbenes against methicillin-resistant Staphylococcus aureus.

Authors:  M Sato; H Tsuchiya; T Miyazaki; M Ohyama; T Tanaka; M Iinuma
Journal:  Lett Appl Microbiol       Date:  1995-10       Impact factor: 2.858

8.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354

9.  Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids.

Authors:  Cristian Soldi; Kellan N Lamb; Richard A Squitieri; Marcos González-López; Michael J Di Maso; Jared T Shaw
Journal:  J Am Chem Soc       Date:  2014-10-21       Impact factor: 15.419

10.  Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C-H insertion of donor/donor carbenes.

Authors:  Leslie A Nickerson; Benjamin D Bergstrom; Mingchun Gao; Yuan-Shin Shiue; Croix J Laconsay; Matthew R Culberson; Walker A Knauss; James C Fettinger; Dean J Tantillo; Jared T Shaw
Journal:  Chem Sci       Date:  2019-11-13       Impact factor: 9.825
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