Literature DB >> 24766317

Enantioselective insertion of a carbenoid carbon into a C-C bond to expand cyclobutanols to cyclopentanols.

Akira Yada1, Shoichiro Fujita, Masahiro Murakami.   

Abstract

When a carbenoid species generated from a tosylhydrazone is reacted with a cyclobutanol in the presence of a chiral rhodium catalyst, a C-C single bond of the cyclobutanol is cleaved, and the carbenoid carbon is inserted therein to furnish a ring-expanded cyclopentanol in an enantioselective manner.

Entities:  

Year:  2014        PMID： 24766317     DOI： 10.1021/ja502229c

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


  11 in total

1.  Rhodium-Catalyzed (4+1) Cycloaddition between Benzocyclobutenones and Styrene-Type Alkenes.

Authors:  Shusuke Ochi; Zining Zhang; Ying Xia; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-30       Impact factor: 16.823

Review 2.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

3.  (4+1) vs (4+2): Catalytic Intramolecular Coupling between Cyclobutanones and Trisubstituted Allenes via C-C Activation.

Authors:  Xuan Zhou; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-10-16       Impact factor: 15.419

4.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419

5.  Rh-catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones.

Authors:  Peng-Hao Chen; Joshua Sieber; Chris H Senanayake; Guangbin Dong
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825

6.  Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Authors:  Xinxin Zheng; Rui Guo; Guozhu Zhang; Dayong Zhang
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

7.  Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds.

Authors:  Gui Chen; Jinshuai Song; Yinghua Yu; Xuesong Luo; Chunsen Li; Xueliang Huang
Journal:  Chem Sci       Date:  2015-12-14       Impact factor: 9.825

8.  Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Authors:  Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal:  Chem Sci       Date:  2017-01-23       Impact factor: 9.825

Review 9.  Uncommon carbene insertion reactions.

Authors:  Ming-Yao Huang; Shou-Fei Zhu
Journal:  Chem Sci       Date:  2021-11-02       Impact factor: 9.825

10.  Silver-Catalyzed Regio- and Stereoselective Formal Carbene Insertion into Unstrained C-C σ-Bonds of 1,3-Dicarbonyls.

Authors:  Zhaohong Liu; Xinyu Zhang; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  iScience       Date:  2018-09-18
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