Stereoselective Formation of Carbon−Carbon Bonds via SN2-Displacement: Synthesis of Substituted Cycloalkyl[b]indoles

Autor:	Richard D. Tillyer, Jean-François Marcoux, and Arlene E. McKeown, Dalian Zhao, Edward J. J. Grabowski, Michael C. Hillier
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Indole test Indoles Ketone Molecular Structure Stereochemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Borane Alkylation Carbon Stereocenter chemistry.chemical_compound chemistry Nucleophile Cyclization Mitsunobu reaction
Zdroj:	The Journal of Organic Chemistry. 70:8385-8394
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo051146p
Popis:	A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b]indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective S(N)2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C1 or C3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::669580a38790abc14246394af15f7786 https://doi.org/10.1021/jo051146p Zobrazit plný text záznamu