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Asymmetric Vinylogous Mukaiyama‐Mannich Reactions of Heterocyclic Siloxy Dienes with Ellman's Fluorinated Aldimines
Author(s) -
Fustero Santos,
Rodenes Miriam,
Román Raquel,
Sedgwick Daniel M.,
Aguado José Enrique,
Soloshonok Vadim A.,
Han Jianlin,
Mei Haibo,
MedioSimon Mercedes,
Barrio Pablo
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900464
Subject(s) - chemistry , aldimine , heteroatom , adduct , furan , pyrrole , mannich reaction , organic chemistry , stereochemistry , medicinal chemistry , ring (chemistry) , catalysis
Vinylogous Mukaiyama Mannich reactions of furan and pyrrole based dienoxy silanes with α‐fluoroalkyl sulfinyl imines provide a powerful synthetic access to a variety of amino fluoroalkyl γ‐butenolide‐type and butyrolactam frameworks with high regio‐ and diastereoselectivity. Anti ‐configured adducts were obtained in all cases, independent of the nature of the heteroatom ( O or N ) present in the dienoxy silane. The absolute configuration of the adducts prepared was unequivocally established by X‐ray crystallographic analysis. It is noteworthy that the introduction of substituents at the γ‐position of the heterocyclic partner allows the generation of adducts bearing chiral quaternary centers.