Das Kondensationsprodukt C13H14O2 aus Salicylal‐aceton und Acetessigester, ein tricyclisches Keton

Kühn, Richard; Weiser, D

doi:10.1002/cber.19550881102

Cited by 9 publications

(1 citation statement)

References 7 publications

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“…The racemic 2,6-methanobenzoxocinone derivative 6 was prepared from salicylideneacetone and ethyl acetoacetate by using the procedure of Kuhn and Weiser. 9 Its chemical resolution was carried out with (ϩ)-(1-phenylethyloxamoyl)hydrazine 7, a carbonyl derivatizing agent 10-13 (Scheme 1). In contrast to previous findings, [10][11][12][13] where the resolution of chiral ketone derivatives with 7 resulted in the two corresponding diastereomers, which could be separated by fractional crystallization, the condensation of rac-6 with this reagent, monitored by TLC, showed the formation of four products of comparable ratio instead of two.…”

Section: Resultsmentioning

confidence: 99%

Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

Kurtán

Baitz-Gács

Májer

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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Section: Resultsmentioning

confidence: 99%

Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

Kurtán

Baitz-Gács

Májer

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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Construction of Chiral Bridged Tricyclic Benzopyrans: Enantioselective Catalytic Diels–Alder Reaction and a One‐Pot Reduction/Acid‐Catalyzed Stereoselective Cyclization

et al. 2014

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An asymmetric two‐step approach to chiral bridged tricyclic benzopyrans, core structures featured in various natural products, is described. In the synthesis, an unprecedented enantioselective catalytic decarboxylative Diels–Alder reaction is developed using readily available coumarin‐3‐carboxylic acids and aldehydes as reactants under mild reaction conditions. Notably, the decarboxylation‐assisted release of the catalyst enables the process to proceed efficiently with high enantio‐ and diastereoselectivity. Furthermore, a one‐pot procedure for either a LiAlH4‐ or NaBH4‐mediated reduction with subsequent acid‐catalyzed intramolecular cyclization of the Diels–Alder adducts was identified for the efficient formation of the chiral bridged tricyclic benzopyrans.

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Das Kondensationsprodukt C₁₃H₁₄O₂ aus Salicylal‐aceton und Acetessigester, ein tricyclisches Keton

Abstract: Die von T. A. Forster und I. M. Heilbron erhaltene Verbindung C13H14O2 ist nicht das Chromen VIII, sondern ein tricyclisches Keton der Formel V, das sich – vergleichbar dem Anhydrid der cis-Hexahydro-isophthalsäure – spannungsfrei konstruieren läßt

Cited by 9 publications

References 7 publications

Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

Resolution and configurational assignment of 3,4,5,6-tetrahydro-2-methyl-2,6-methano-2H-1-benzoxocine derivatives

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Construction of Chiral Bridged Tricyclic Benzopyrans: Enantioselective Catalytic Diels–Alder Reaction and a One‐Pot Reduction/Acid‐Catalyzed Stereoselective Cyclization

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