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Literature DB >> 28466963

A Rhodium(II)-Catalyzed Formal [4+1]-Cycloaddition toward Spirooxindole Pyrrolone Construction Employing Vinyl Isocyanates as 1,4-Dipoles.

Jennifer L Meloche¹, Brandon L Ashfeld¹.

Abstract

A RhII -catalyzed, formal [4+1]-cycloaddition between diazooxindoles as electrophilic C1 synthons and 1,3-heterodienes for the construction of spirooxindole pyrrolones is described. Employing vinyl isocyanates as 1,4-dipoles, the cycloannulation occurs under relatively mild conditions and provides the corresponding pyrrolones in good to excellent yields.

Entities: Chemical Gene

Keywords: [4+1]-cycloadditions; cyclopropane rearrangements; diazooxindoles; spirooxindole alkaloids; vinyl isocyanates

Year: 2017 PMID： 28466963 DOI： 10.1002/anie.201701147

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

3 in total

1. An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh^II-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors: Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal: Chem Sci Date: 2018-02-19 Impact factor: 9.825

2. Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction.

Authors: Hui-Xuan Chen; Yaqi Zhang; Yuyang Zhang; Xuefeng He; Zhen-Wei Zhang; Hao Liang; Wenhuan He; Xiaoding Jiang; Xiangmeng Chen; Liqin Qiu
Journal: RSC Adv Date: 2018-11-01 Impact factor: 4.036

3. Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors: Amarendar Reddy Maddirala; Peter R Andreana
Journal: Beilstein J Org Chem Date: 2018-04-18 Impact factor: 2.883

3 in total

A Rhodium(II)-Catalyzed Formal [4+1]-Cycloaddition toward Spirooxindole Pyrrolone Construction Employing Vinyl Isocyanates as 1,4-Dipoles.

1. An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

2. Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction.

3. Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

1. An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective Rh^II-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.