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Formal Desymmetrization by a “Mitsunobu Trick” − Enantiomerically Purecis-3,4-DihydroxypyrrolineN-Oxides for the Enantiodivergent Synthesis of Trihydroxyindolizidines

1998; Wiley; Volume: 1998; Issue: 3 Linguagem: Inglês

10.1002/(sici)1099-0690(199803)1998

1434-193X

Stefano Cicchi, J. JUN. NUNES, Andrea Goti, Alberto Brandi,

Cyclopropane Reaction Mechanisms

European Journal of Organic ChemistryVolume 1998, Issue 3 p. 419-421 Short Communication Formal Desymmetrization by a “Mitsunobu Trick” − Enantiomerically Pure cis-3,4-Dihydroxypyrroline N-Oxides for the Enantiodivergent Synthesis of Trihydroxyindolizidines Stefano Cicchi, Stefano Cicchi Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA) − C.N.R, Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Fax: (internat.) + 39(0)55/2476964Search for more papers by this authorJosé Nunes Jr., José Nunes Jr. Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA) − C.N.R, Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Fax: (internat.) + 39(0)55/2476964Search for more papers by this authorAndrea Goti, Andrea Goti [email protected] Search for more papers by this authorAlberto Brandi, Alberto Brandi [email protected] Search for more papers by this author Stefano Cicchi, Stefano Cicchi Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA) − C.N.R, Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Fax: (internat.) + 39(0)55/2476964Search for more papers by this authorJosé Nunes Jr., José Nunes Jr. Centro di Studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA) − C.N.R, Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Fax: (internat.) + 39(0)55/2476964Search for more papers by this authorAndrea Goti, Andrea Goti [email protected] Search for more papers by this authorAlberto Brandi, Alberto Brandi [email protected] Search for more papers by this author First published: March 1998 https://doi.org/10.1002/(SICI)1099-0690(199803)1998:3 3.0.CO;2-VCitations: 20AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract A protocol is presented for a completely enantioselective formal desymmetrization of Cs-symmetric diols by monoprotection of the corresponding enantiopure C2 diols, followed by an inversion of configuration by a Mitsunobu reaction (“Mitsunobu trick”). Its application to the unprecedented synthesis of enantiopure cis-3,4-dihydroxypyrroline N-oxides, employed in the enantiodivergent synthesis of two selectively protected 1,2,7-trihydroxyindolizidines, is also reported. References 1 [1a] A. Brandi, S. Cicchi, F. M. Cordero, R. Frignoli, A. Goti, S. Picasso, P. Vogel, J. Org. Chem. 1995, 60, 6806–6812. 10.1021/jo00126a033 CASWeb of Science®Google Scholar [1b] – A. Goti, F. Cardona, A. Brandi, S. Picasso, P. Vogel, Tetrahedron: Asymmetry 1996, 7, 1659–1674. 10.1016/0957-4166(96)00200-5 CASWeb of Science®Google Scholar [1c] – A. Goti, F. Cardona, A. 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