Literature DB >> 23046060

Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.

Alexander F G Goldberg1, Nicholas R O'Connor, Robert A Craig, Brian M Stoltz.   

Abstract

Isocyanates, isothiocyanates, and carbodiimides are effective substrates in (3 + 2) cycloadditions with donor-acceptor cyclopropanes for the synthesis of five-membered heterocycles. These reactions exhibit a broad substrate scope, high yields, and well-defined chemoselectivity. Discussed herein are the implications of Lewis acid choice on the stereochemical outcome and the reaction mechanism.

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Year:  2012        PMID： 23046060      PMCID： PMC3490221          DOI： 10.1021/ol302494n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

1.  FeCl3 promoted highly regioselective [3 + 2] cycloaddition of dimethyl 2-vinyl and aryl cyclopropane-1,1-dicarboxylates with aryl isothiocyanates.

Authors:  Huina Wang; Wei Yang; Hong Liu; Wei Wang; Hao Li
Journal:  Org Biomol Chem       Date:  2012-05-31       Impact factor: 3.876

2.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

3.  Total synthesis of (+)-isatisine A.

Authors:  Avedis Karadeolian; Michael A Kerr
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-01       Impact factor: 15.336

Review 4.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

5.  Enantiospecific Sn(II)- and Sn(IV)-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes.

Authors:  Patrick D Pohlhaus; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

6.  A palladium-catalyzed vinylcyclopropane (3+2) cycloaddition approach to the Melodinus alkaloids.

Authors:  Alexander F G Goldberg; Brian M Stoltz
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

7.  Asymmetric synthesis of (+)-polyanthellin A.

Authors:  Matthew J Campbell; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

8.  The cycloaddition of nitrones with homochiral cyclopropanes.

Authors:  Katarina Sapeta; Michael A Kerr
Journal:  J Org Chem       Date:  2007-10-06       Impact factor: 4.354

9.  Scope and mechanism for lewis acid-catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes: evidence for a stereospecific intimate ion pair pathway.

Authors:  Patrick D Pohlhaus; Shanina D Sanders; Andrew T Parsons; Wei Li; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

10.  Catalytic enantioselective synthesis of tetrahydrofurans: a dynamic kinetic asymmetric [3 + 2] cycloaddition of racemic cyclopropanes and aldehydes.

Authors:  Andrew T Parsons; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419
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  8 in total

1.  Stereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes.

Authors:  Robert A Craig; Nicholas R O'Connor; Alexander F G Goldberg; Brian M Stoltz
Journal:  Chemistry       Date:  2014-03-06       Impact factor: 5.236

2.  I2-mediated Csp2-P bond formation via tandem cyclization of o-alkynylphenyl isothiocyanates with organophosphorus esters.

Authors:  Yang Liu; Wenjin Wu; Xiaoyan Sang; Yu Xia; Guojian Fang; Wenyan Hao
Journal:  RSC Adv       Date:  2022-06-20       Impact factor: 4.036

3.  Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors:  Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal:  European J Org Chem       Date:  2021-08-25

4.  Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates.

Authors:  Rong Zeng; Peng-Hao Chen; Guangbin Dong
Journal:  ACS Catal       Date:  2015-12-30       Impact factor: 13.084

5.  Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

Authors:  Haipan Zhu; Peile Du; Jianjun Li; Ziyang Liao; Guohua Liu; Hao Li; Wei Wang
Journal:  Beilstein J Org Chem       Date:  2016-06-29       Impact factor: 2.883

6.  Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.

Authors:  Ivan A Andreev; Nina K Ratmanova; André U Augustin; Olga A Ivanova; Irina I Levina; Victor N Khrustalev; Daniel B Werz; Igor V Trushkov
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

7.  Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines.

Authors:  Gwyndaf A Oliver; Maximilian N Loch; André U Augustin; Pit Steinbach; Mohammed Sharique; Uttam K Tambar; Peter G Jones; Christoph Bannwarth; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-29       Impact factor: 16.823

8.  Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Authors:  Vincent Pirenne; Emma G L Robert; Jerome Waser
Journal:  Chem Sci       Date:  2021-05-05       Impact factor: 9.825
  8 in total

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