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Journal article
Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ‐Carbolines
Angewandte Chemie (International ed.), v 56(15), pp 4310-4313
03 Apr 2017
PMID: 28295938
Abstract
Isocyanides are exceptional building blocks, the wide deployment of which in multicomponent and metal‐insertion reactions belies their limited availability. The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this deficiency. An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to β‐ and β,β‐disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri‐ and tetra‐substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three‐step synthesis of γ‐carboline N‐methyl ingenine B.
Conjugate addition of diverse organometallic compounds to sulfonyl‐substituted alkenyl isocyanides overcomes the historical challenge of rapidly assembling complex isocyanides that retain the isocyanide functionality. The strategy affords complex isocyanides that are poised for elaboration into heterocycles, as illustrated by the three‐step synthesis of N‐methyl ingenine B.
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Details
- Title
- Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ‐Carbolines
- Creators
- Sergiy V. Chepyshev - Drexel UniversityJ. Armando Lujan‐Montelongo - Centro de Investigación y de Estudios Avanzados (Cinvestav)Allen Chao - Drexel UniversityFraser F. Fleming - Drexel University
- Publication Details
- Angewandte Chemie (International ed.), v 56(15), pp 4310-4313
- Publisher
- Wiley
- Number of pages
- 4
- Grant note
- 10.13039/100000002 (2R15AI051352-04)
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000397599500042
- Scopus ID
- 2-s2.0-85014911455
- Other Identifier
- 991019169582404721
InCites Highlights
Data related to this publication, from InCites Benchmarking & Analytics tool:
- Collaboration types
- Domestic collaboration
- International collaboration
- Web of Science research areas
- Chemistry, Multidisciplinary