0000000001307290
AUTHOR
Alvaro Sanz-vidal
ChemInform Abstract: Gold-Catalyzed Povarov-Type Reaction of Fluorinated Imino Esters and Furans.
A gold-catalyzed Povarov-type reaction of fluorinated imino esters and furans is described. The process, which takes place in dichoromethane at room temperature, gives rise to novel fluorinated tetrahydrofuran-fused tetrahydroquinolines in good yields and moderate levels of diastereoselectivity in a very simple manner. The reported examples expand the versatility of the Povarov reaction to unprecedented fluorinated substrates, generating scaffolds that contain quaternary α-amino acid units.
Highly convergent total synthesis of (+)-anaferine and (−)-dihydrocuscohygrine
A unified and highly convergent total synthesis of anaferine and dihydrocuscohygrine alkaloids has been devised, taking advantage of the dual role of N-sulfinyl amines as nucleophilic nitrogen sources and chiral auxiliaries. A bidirectional cross metathesis reaction followed by a double intramolecular aza-Michael reaction led us to create the whole skeleton of the natural products in a very simple manner.
Gold-Catalyzed Povarov-Type Reaction of Fluorinated Imino Esters and Furans
A gold-catalyzed Povarov-type reaction of fluorinated imino esters and furans is described. The process, which takes place in dichoromethane at room temperature, gives rise to novel fluorinated tetrahydrofuran-fused tetrahydroquinolines in good yields and moderate levels of diastereo-selectivity in a very simple manner. The reported examples expand the versatility of the Povarov reaction to unprecedented fluorinated substrates, generating scaffolds that contain quaternary alpha-amino acid units.
Asymmetric Vinylogous Mannich-Type Addition of α,α-Dicyanoalkenes to α-Fluoroalkyl Sulfinyl Imines
Abstract. The asymmetric vinylogous Mannich reaction (AVMR) of alfa,alfa-dicyanoalkenes with alfa-fluoroalkyl sulfinyl imines has been successfully accomplished. This transformation is unprecedented with fluorinated imines at the same time as the use of dicyanoalkenes in AVMR has been scarcely reported. Several fluorinated sulfinyl imines are compatible with the process, which gaves access to a family of chiral fluorinated amines with excellent level of stereocontrol. Interestingly, the selectivity found in our protocol is reverse to that encountered in analogous AVMR previously reported. Additionally, the synthetic applicability of the addition products has been exemplified with several tr…
Unexpected metal-free synthesis of trifluoromethyl arenes via tandem coupling of dicyanoalkenes and conjugated fluorinated sulfinyl imines
A novel strategy for the synthesis of policyclic trifluoromethyl arenes has been devised. It involves a DBU-promoted tandem cycloaromatization reaction of dicyanoalkenes and fluorinated conjugated sulfinyl imines. This unprecedented transformation is a metal-free and air-tolerant process that takes place from readily available starting materials under mild reaction conditions.
CCDC 1989940: Experimental Crystal Structure Determination
Related Article: Alvaro Sanz-Vidal, Daniel Gaviña, Lia Sotorríos, Enrique Gómez-Bengoa, Fernando López Ortiz, María Sánchez-Roselló, Carlos del Pozo|2021|Chem.Commun.|57|8023|doi:10.1039/D1CC03161A
CCDC 1989936: Experimental Crystal Structure Determination
Related Article: Alvaro Sanz-Vidal, Daniel Gaviña, Lia Sotorríos, Enrique Gómez-Bengoa, Fernando López Ortiz, María Sánchez-Roselló, Carlos del Pozo|2021|Chem.Commun.|57|8023|doi:10.1039/D1CC03161A