ChemInform Abstract: Catalytic Asymmetric Inverse‐Electron‐Demand Oxa‐Diels—Alder Reaction of in situ Generated ortho‐Quinone Methides with 3‐Methyl‐2‐vinylindoles.

Abstract

The first examples of an asymmetric inverse-electron demand oxa-Diels-Alder reaction of ortho-quinone methides, generated in situ from ortho-hydroxybenzyl alcohols, is described using 3-methyl-2-vinylindoles as dienophiles. The process produces enantioenriched chromanes with three adjacent stereogenic centers. -(ZHAO, J.-J.; SUN, S.-B.; HE, S.-H.; WU, Q.; SHI*, F.; Angew. Chem., Int. Ed. 54 (2015) 18, 5460-5464, http://dx.doi.org/10.1002/anie.201500215 ; Sch. Chem. Chem. Eng., Jiangsu Norm. Univ., Jiangsu, Xuzhou 221116, Peop. Rep. China; Eng.) -Mais 36-172

Asymmetric synthesis and biological activities of natural product (+)-balasubramide and its derivatives

“…In recent years, as a catalytic method with the same status of enzyme catalysis and metal catalysis, asymmetric catalysis has been an important tool for building chiral molecular scaffold owing to the high efficiency and selectivity Wang et al 2015;Woźniak et al 2015;Zhao et al 2015). Our group initially reported a model reaction of cinnamaldehyde with organocatalyst, a diphenyl prolinol TES ether, to synthesize methyl (2S,3R)-(+)-3-phenyloxirane-2-carboxylate (1h) via a one-pot reaction with 73% yield and 95% enantioselectivity (Xuan et al 2013).…”