Domino Reactions in Organic Synthesis

Tietze, L. F.

doi:10.1002/9783527609925

Cited by 1,649 publications

(703 citation statements)

References 272 publications

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“…We believe that the change in base from piperidine to Et 3 N may shift the mechanism from the Knoevenagel mechanism (iminium formation) to the Hann-Lapworth mechanism (β-hydroxy ester formation). 50 This shift in mechanistic pathway should eliminate the possibility for enamine formation and consequently epimerization. We were pleased to see that reaction using either pyridine or Et 3 N provided solely the cis-diastereomer.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation

Huang

Bergmeier

2008

Tetrahedron

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A diastereoselective approach to 3,7,8-trisubstituted cis-decahydroquinolines is described. This ring system forms the core of rings B and E of the norditerpenoid alkaloid methyllycaconitine. This approach starts with a known disubsituted cyclohexene. The remaining carbons are attached via a Knoevenagel condensation followed by an intramolecular lactam formation. The stereochemistry of the substituents is controlled by the cis-substitution of the starting cyclohexene ring.

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Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of a highly substituted cis-decahydroquinoline via a Knoevenagel condensation

Huang

Bergmeier

2008

Tetrahedron

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“…[31,32] Originally we isolated the dimer 31 only in trace amounts as a side product. Running the reaction with stoichiometric amounts of Au catalyst gave the dimer 31 For the oxidative coupling two path ways are conceivable: First, the Au complex C (Scheme 10) undergoes a di merization after the cyclization.…”

Section: Oxidative Coupling Reactions Using Catalytic Amounts Of Aumentioning

confidence: 99%

Oxidative Coupling Reactions with Gold

Wegner

2009

Chimia

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.Abstract: Oxidative coupling reactions are a very powerful tool for the construction of e.g. biaryl compounds, especially because typically no functionalization of the coupling partners is necessary. The use of Au for this transformation is particularly attractive since usually no special precautions to exclude moisture or air are necessary. Furthermore, the combination of oxidative coupling reactions with other Au-catalyzed reactions enables the rapid and efficient construction of molecular complexity, e.g. the constructions of dicoumarins via a domino cyclization oxidative coupling reaction.

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“…6 In contrast to Wittig type reactions, Knoevenagel condensation is an atom-economic and cleaner tool for constructing the α,β-unsaturated structure unit from a carbonyl and an active methylene components. 13 Knoevenagel reactions can be promoted by solid supported reagents, 14 fluoride anion, 15 and KF/Al 2 O 3 16 and the generation of large amounts of salts at the end of the synthesis as well as the use of stoichiometric strong bases can be avoided.…”

Section: Introductionmentioning

confidence: 99%