Asymmetric Phase‐Transfer Catalysis in Organic Synthesis

Shen, Li; Ma, Jun‐An

doi:10.1002/9783527675906.ch12

Cited by 8 publications

(1 citation statement)

References 260 publications

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“…Simple operational procedures, ease of catalyst separation and recycling, and absence of metal impurities and water sensitive reagents are some of the advantages provided by PTC, that have led to broad application both in small scale and industrial low cost, high performing, and environmentally benign processes [24][25][26][27][28]. The beginning of XXI century, in particular, has seen the explosion of the asymmetric PTC [29][30][31][32][33][34][35]. The inorganic base initiated reactions, involving the deprotonation of a moderately acidic substrate with the generation of a reacting organic anion, are the most commonly used phase transfer catalyzed processes in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Vinylogous and Arylogous Stereoselective Base-Promoted Phase-Transfer Catalysis

D’Amato

Sala

2021

Catalysts

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Vinylogous enolate and enolate-type carbanions, generated by deprotonation of α,β-unsaturated compounds and characterized by delocalization of the negative charge over two or more carbon atoms, are extensively used in organic synthesis, enabling functionalization and C–C bond formation at remote positions. Similarly, reactions with electrophiles at benzylic and heterobenzylic position are performed through generation of arylogous and heteroarylogous enolate-type nucleophiles. Although widely exploited in metal-catalysis and organocatalysis, it is only in recent years that the vinylogy and arylogy principles have been translated fruitfully in phase-transfer catalyzed processes. This review provides an overview of the methods developed to date, involving vinylogous and (hetero)arylogous carbon nucleophiles under phase-transfer catalytic conditions, highlighting main mechanistic aspects.

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