Organolead-mediated arylation of allyl β-ketoesters: a selective synthesis of isoflavanones and isoflavones
01 Jan 1993-Journal of The Chemical Society-perkin Transactions 1 (The Royal Society of Chemistry)-Iss: 15, pp 1729-1735
TL;DR: Arylation of 3-allyloxy carbonylchroman-4-ones with aryllead (IV) triacetates followed by selective catalytic deally-oxycarbonylation affords isoflavanones or isoflavones in high overall yields as mentioned in this paper.
Abstract: Arylation of A- ring substituted and unsubstituted 3-allyloxycarbonylchroman-4-ones with aryllead (IV) triacetates followed by selective catalytic deallyloxycarbonylation affords isoflavanones or isoflavones in high overall yields. The highest yield in the arylation step was observed in the reaction of 5,7-dimethoxychroman-4-one with the more hindered 2,4,6-trimethoxyphenyllead triacetate.
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TL;DR: Stereochemical alchemy!
Abstract: Stereochemical alchemy! Racemic allyl β-ketoesters allow the regiocontrolled formation of enolates, where the same catalyst is intimately involved in both the stereoablative (C-C bond-breaking) and stereoselective (C-C bond-forming) steps. This mechanistic and practical insight led to the formation of multiple quaternary carbon stereocenters in a single cascade reaction (see scheme).
311 citations
106 citations
TL;DR: In this article, the tandem Michael addition was applied to cyclohexanones with high diastereo and enantioselectivity, achieving up to 99% de and 92% ee.
105 citations
TL;DR: In this paper, the PdCl2(Ph3P)2-Cs2CO3 reaction system was used for intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group.
51 citations
TL;DR: The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions.
Abstract: Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ-quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions.
48 citations
References
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Book•
01 Jan 1962
TL;DR: The chemistry of flavonoid compounds will lead you to love reading starting from now and will guide you to even the prestige stage of the life.
Abstract: We may not be able to make you love reading, but the chemistry of flavonoid compounds will lead you to love reading starting from now. Book is the window to open the new world. The world that you want is in the better stage and level. World will always guide you to even the prestige stage of the life. You know, this is some of how reading will give you the kindness. In this case, more books you read more knowledge you know, but it can mean also the bore is full.
678 citations
TL;DR: C-acylation of lithium enolates by methyl cyanoformate provides high yields of β-keto esters under mild conditions and with 100% regioselectivity as mentioned in this paper.
266 citations
TL;DR: In this article, the synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.
Abstract: The synthesis of isoflavone derivatives by means of palladium-catalyzed cross-coupling reaction between 3-bromochromones and arylboronic acids or its butyl esters is described.
118 citations
88 citations
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