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Diastereoselective ...
Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones : A Mechanistic Investigation
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- Angelin, Marcus (author)
- KTH,Kemi
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- Rahm, Martin (author)
- KTH,Kemi
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- Fischer, Andreas (author)
- KTH,Kemi
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- Brinck, Tore (author)
- KTH,Kemi
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- Ramström, Olof (author)
- KTH,Kemi
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(creator_code:org_t)
- 2010-08-06
- 2010
- English.
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 75:17, s. 5882-5887
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Teoretisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Theoretical Chemistry (hsv//eng)
Keyword
- DYNAMIC COMBINATORIAL CHEMISTRY
- DIELS-ALDER REACTIONS
- ASYMMETRIC-SYNTHESIS
- DRUG DISCOVERY
- DERIVATIVES
- RECEPTOR
- ISOINDOLOBENZAZEPINE
- 2-CYANOBENZALDEHYDE
- ISOINDOLIN-1-ONES
- AUXILIARIES
- Organic chemistry
- Organisk kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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