Literature DB >> 30188137

Asmic: An Exceptional Building Block for Isocyanide Alkylations.

Embarek Alwedi1, J Armando Lujan-Montelongo1, Bhaskar R Pitta1, Allen Chao1, Rodrigo Cortés-Mejía1, Jorge M Del Campo1, Fraser F Fleming1.   

Abstract

Asmic addresses the long-standing challenge of alkylating isocyanides, providing access to isocyanides with diverse substitution patterns. The o-anisylsulfanyl group serves a critical dual role by facilitating deprotonation-alkylation and providing a latent nucleophilic site through an unusual arylsulfanyl-lithium exchange.

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Year:  2018        PMID: 30188137      PMCID: PMC6172042          DOI: 10.1021/acs.orglett.8b02574

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


  13 in total

Review 1.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

2.  Brønsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide.

Authors:  Răzvan C Cioc; Peter Schuckman; Hans D Preschel; Tjøstil Vlaar; Eelco Ruijter; Romano V A Orru
Journal:  Org Lett       Date:  2016-07-12       Impact factor: 6.005

3.  Stability and reactivity control of carbenoids: recent advances and perspectives.

Authors:  Viktoria H Gessner
Journal:  Chem Commun (Camb)       Date:  2016-08-08       Impact factor: 6.222

Review 4.  Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors:  Martin J Schnermann; Ryan A Shenvi
Journal:  Nat Prod Rep       Date:  2015-04       Impact factor: 13.423

5.  Quantitative data on the effects of alkyl substituents and Li-O and Li-N chelation on the stability of secondary alpha-oxy-organolithium compounds.

Authors:  Pablo Monje; Paula Graña; M Rita Paleo; F Javier Sardina
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

6.  Arylthio-metal exchange of α-arylthioalkanenitriles.

Authors:  Dinesh Nath; Melanie C Skilbeck; Iain Coldham; Fraser F Fleming
Journal:  Org Lett       Date:  2013-12-12       Impact factor: 6.005

7.  Novel benzodiazepine receptor partial agonists: oxadiazolylimidazobenzodiazepines.

Authors:  F Watjen; R Baker; M Engelstoff; R Herbert; A MacLeod; A Knight; K Merchant; J Moseley; J Saunders; C J Swain
Journal:  J Med Chem       Date:  1989-10       Impact factor: 7.446

8.  Preparation of enantiopure chiral amino-[D1]methyllithium compounds and determination of their micro- and macroscopic configurational stabilities.

Authors:  Dagmar C Kapeller; Friedrich Hammerschmidt
Journal:  Chemistry       Date:  2009-06-02       Impact factor: 5.236

Review 9.  Isocyanide-based multicomponent reactions in drug discovery.

Authors:  Irini Akritopoulou-Zanze
Journal:  Curr Opin Chem Biol       Date:  2008-03-14       Impact factor: 8.822

10.  Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.

Authors:  Răzvan C Cioc; Hans D Preschel; Gydo van der Heijden; Eelco Ruijter; Romano V A Orru
Journal:  Chemistry       Date:  2016-04-26       Impact factor: 5.236

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  1 in total

1.  Acetonitrile-Hexane Extraction Route to Pure Sulfonium Salts.

Authors:  Bilal Altundas; Chepuri V Suneel Kumar; Fraser F Fleming
Journal:  ACS Omega       Date:  2020-05-29
  1 in total

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