Catalytic Enantioselective Desymmetrizations of Prochiral Dienone Systems

Gaëtan Maertens; Marc-André Ménard; Sylvain Canesi

doi:10.1055/s-0033-1341224

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(12): 1573-1582
DOI: 10.1055/s-0033-1341224

short review

Catalytic Enantioselective Desymmetrizations of Prochiral Dienone Systems

Gaëtan Maertens

Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada Fax: +1(514)9874054 eMail: canesi.sylvain@uqam.ca

,

Marc-André Ménard

Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada Fax: +1(514)9874054 eMail: canesi.sylvain@uqam.ca

,

Sylvain Canesi*

Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, Québec, H3C 3P8, Canada Fax: +1(514)9874054 eMail: canesi.sylvain@uqam.ca

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Abstract

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Abstract

This article describes a number of catalytic methods for enantioselectively desymmetrizing prochiral dienone systems. The core structures obtained using these methodologies appear in several bioactive natural products, and the processes appear to be effective tools for producing key intermediates in the synthesis of complex structures.

1 Introduction

2 Covalent Organocatalyzed Desymmetrizations

2.1 Formation of Chiral Enamines

2.2 The Stetter Reaction

2.3 Other Covalent Desymmetrizations

3 Noncovalent Organocatalyzed Desymmetrizations

4 Transition Metals

5 Cycloadditions

6 Conclusion

Key words

prochiral dienone - phenol dearomatization - desymmetrization - enantioselective catalysis

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Referenzen

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