Pregled bibliografske jedinice broj: 1153269
Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid- Catalyzed Cycloaddition
Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid- Catalyzed Cycloaddition // Journal of the American Chemical Society, 143 (2021), 30; 11611-11619 doi:10.1021/jacs.1c04648 (međunarodna recenzija, članak, znanstveni)
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Naslov
Enantioselective and Diastereodivergent Synthesis
of Spiroindolenines via Chiral Phosphoric Acid-
Catalyzed Cycloaddition
Autori
Varlet, Thomas ; Matišić, Mateja ; Van Elslande, Elsa ; Neuville, Luc ; Gandon, Vincent ; Masson, Géraldine
Izvornik
Journal of the American Chemical Society (0002-7863) 143
(2021), 30;
11611-11619
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Stereoselectivity, Enantioselective synthesis, Catalysts, Thermodynamics, Molecular structure
Sažetak
A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1, 3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and - oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
- MEDLINE
- Nature Index
