Organocatalytic Enantioselective Friedel-Crafts Reaction of Naphthol with β,γ-Unsaturated α-Keto Esters
نویسندگان
چکیده
منابع مشابه
Squaramide-catalyzed enantioselective Friedel-Crafts reaction of indoles with imines.
Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85-96% yields and 84-96% ees.
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A Michael-type reaction of β,γ-unsaturated α-keto ester and α-nitro ketone was established. With a thiourea catalyst derived from cinchona alkaloid, the reactions afford products in 47-94% yields with 68-96% ee.
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We disclose herein a highly enantioselective de novo-synthesis of chiral 1-cyclopentenyl-α-keto esters starting from a simple bis-silyl-1,3-dienediolate and α,β-unsaturated aldehydes via a domino vinylogous Michael-intramolecular Knoevenagel-type condensation. The cyclopentenes proved to be highly versatile and were readily converted into various structural motifs.
متن کاملDevelopment of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes.
LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and -pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both, syn and anti Mukaiyama-Michael products with high levels of enantioselectivity. This strategy allows for the generation of chemically useful 1,5-dicarbonyl systems and again highlights the utility of organocatalysis.
متن کاملNHC organocatalytic formal LUMO activation of α,β-unsaturated esters for reaction with enamides.
a,b-Unsaturated carbonyl compounds are basic building blocks in organic synthesis. Lewis acid catalysts bearing chiral ligands have traditionally been used for the asymmetric catalytic activation of this class of molecules as Michael acceptors. Indeed, Lewis acid catalysis continues to be a powerful approach in which innovative solutions are still emerging. Representative examples of chiral Lew...
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ژورنال
عنوان ژورنال: Bulletin of the Korean Chemical Society
سال: 2013
ISSN: 0253-2964
DOI: 10.5012/bkcs.2013.34.12.3539