Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters

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URI: http://hdl.handle.net/10347/16981
E-ISSN: 1099-0690
DOI: 10.1002/ejoc.201101427

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2012

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Wiley
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Abstract

A one‐pot, enantioselective strategy for the dearomatization–annulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is presented. This methodology is based on the reaction of bisenolates, prepared by treating aromatic diesters with trialkyltin lithium reagents, which involves a stanna‐Brook rearrangement, with 1,ω‐dihaloalkanes and other biselectrophiles. We have also developed experimental conditions for performing these reactions with substoichiometric amounts of the required tin reagent by in situ recycling of Me6Sn2 into Me3SnLi with excess lithium metal, and provide a study of the scope and limitations of this synthetic methodology

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This is the peer reviewed version of the following article: Pérez-Vázquez, J., Veiga, A., Prado, G., Sardina, F., & Paleo, M. (2012). Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters. European Journal Of Organic Chemistry, 2012(5), 975-987, which has been published in final form at https:// doi.org/10.1002/ejoc.201101427. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions

Keywords

Dearomatization-alkylation| Stanna-Brook| Bis-enolate| Annulation| Enantioselective alkylation

Bibliographic citation

Pérez-Vázquez, J., Veiga, A., Prado, G., Sardina, F., & Paleo, M. (2011). Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters. European Journal Of Organic Chemistry, 2012(5), 975-987. doi: 10.1002/ejoc.201101427

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Financial support from Spanish MCYT (fellowship to A. V.) and Xunta de Galicia (Grants 10PXIB209113PR and 10PXIB209155PR) is gratefully acknowledged

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© 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving

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