Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamine

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Title: Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamine
Authors: Anton-Torrecillas, Cintia | Gonzalez-Gomez, Jose C.
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Chiral phenanthroindolizidines | Homoallylic sulfinamines | Asymmetric synthesis
Knowledge Area: Química Orgánica
Issue Date: 29-Jul-2014
Publisher: Royal Society of Chemistry
Citation: Organic & Biomolecular Chemistry. 2014, 12: 7018-7025. doi:10.1039/C4OB01133C
Abstract: An efficient stereocontrolled preparation of chiral phenanthroindolizidines is detailed. The synthesis relies on the stereoselective indium-mediated allylation of 2-(phenanthren-9-yl)acetaldehyde derivatives with chiral tert-butylsulfinamide. Chemoselective transformations from the corresponding homoallylic sulfinamine allow the synthesis of the phenanthroindolizidines in only three synthetic operations, without any detectable racemization. Following this procedure, the synthesis of natural (−)-tylophorine was successfully accomplished.
Sponsor: We thank the Spanish Ministerio de Ciencia e Innovación for their financial support (CTQ2011-24165). C. A.-T. thanks the ISO for a grant.
ISSN: 1477-0520 (Print) | 1477-0539 (Online)
DOI: 10.1039/C4OB01133C
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Royal Society of Chemistry 2014
Peer Review: si
Publisher version:
Appears in Collections:INV - CESO - Artículos de Revistas

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