RT Journal Article
T1 Enantioselective Annulation Reactions of Bisenolates Prepared Through Dearomatization Reactions of Aromatic and Heteroaromatic Diesters
A1 Pérez-Vázquez, Jaime
A1 Veiga, Alberte X.
A1 Prado, Gustavo
A1 Sardina López, Francisco Javier
A1 Paleo Pillado, María Rita
K1 Dearomatization-alkylation
K1 Stanna-Brook
K1 Bis-enolate
K1 Annulation
K1 Enantioselective alkylation
AB 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
PB Wiley
YR 2012
FD 2012
LK http://hdl.handle.net/10347/16981
UL http://hdl.handle.net/10347/16981
LA eng
NO 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
NO 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 PreparedThrough Dearomatization Reactions of Aromatic and Heteroaromatic Diesters. European Journal OfOrganic 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 andConditions for Use of Self-Archived Versions
NO Financial support from Spanish MCYT (fellowship to A. V.) and Xunta de Galicia (Grants 10PXIB209113PR and 10PXIB209155PR) is gratefully acknowledged
DS Minerva
RD 30 abr 2026