Phase-transfer catalyzed asymmetric epoxidation of chalcones using chiral crown ethers derived from d-glucose, d-galactose, and d-mannitol

Bakó, Tibor; Bakó, Péter; Keglevich, György; Petra, Bombicz; Kubinyi, Miklós; Pál, Krisztina; Bodor, Sándor; Makó, Attila; Tőke, Lásʐló

doi:10.1016/j.tetasy.2004.03.029

Cited by 59 publications

(15 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…15,17 The starting compounds for the synthesis of D-mannitol-based macrocycles were 1,2:5,6-di-O-isopropylidene-D-mannitol, 1,2:5,6-di-O-diphenylmethylidene-D-mannitol (3), and 1,2:5,6-di-Ocyclohexylidene-D-mannitol (4). 15,17 The starting compounds for the synthesis of D-mannitol-based macrocycles were 1,2:5,6-di-O-isopropylidene-D-mannitol, 1,2:5,6-di-O-diphenylmethylidene-D-mannitol (3), and 1,2:5,6-di-Ocyclohexylidene-D-mannitol (4).…”

Section: Synthesismentioning

confidence: 99%

“…5 This binaphthyl-type crown ether was a synthetic compound. [16][17][18] These limited results encouraged us to investigate also the catalytic effect of the mannitol-based 18-crown-6 type macrocycles and the monoaza-15-crown-5 type lariat ethers. Crown ethers with carbohydrate moieties form a special group of optically active macrocycles, which can be used as phase transfer catalysts.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of d‐mannitol‐based crown ethers and their application as catalyst in asymmetric phase transfer reactions

et al. 2017

Self Cite

View full text Add to dashboard Cite

A few new d-mannitol-based monoaza-15-crown-5 type chiral lariat ethers and 18-crown-6 type macrocycles were synthesized. These crown compounds were used as phase transfer catalysts in asymmetric Michael addititons and in a Darzens condensation under mild conditions to afford the corresponding products in a few cases in good to excellent enantioselectivities. In the Michael addition of diethyl acetoxymalonate to trans-chalcone, in the addition of diethyl acetamidomalonate to ß-nitrostyrene, in the reaction of diethyl bromomalonate with benzylidene malononitriles, in the cyclopropanation reaction of diethyl bromomalonate and 2-benzylidene-1,3-indandione, and in the Darzens condensation of α-chloroacetophenone with benzaldehyde, maximum enantioselectivities of 39%, 65%, 99%, 56%, and 62%, respectively, were obtained in the presence of the d-mannitol-based macrocycles as the catalysts.

show abstract

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of d‐mannitol‐based crown ethers and their application as catalyst in asymmetric phase transfer reactions

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…[47][48][49][50][51][52][53][54] These SAC ethers were also used in asymmetrical epoxidation of chalcones (ee up to 99%) [55][56][57][58] and Darzens condensation of 2-chloro-1-phenyl(hetaryl)ethanones 24 with aryl aldehydes 25 (ee up to 86%) 59 (Scheme 3). These macrocycles are particularly useful as efficient, chiral, phase-transfer catalysts that permit the Michael addition of 2-nitropropane to chalcones 21 to be executed with high asymmetrical induction (with ee up to 95%).…”

Section: Nitrogen-containing Carbohydrate-based Macrocyclesmentioning

confidence: 99%

Nitrogen-Containing Macrocycles Having a Carbohydrate Scaffold

Potopnyk¹,

Jarosz²

2014

Advances in Carbohydrate Chemistry and Biochemistry

View full text Add to dashboard Cite

“…Bako et al [34][35][36][37][38][39][40][41][42][43][44][45][46][47] reported the synthesis of some Nsubstituted chiral monoaza-15-crown-5 compounds anellated to glucose, galactose, mannose or derived from D-mannitol by cyclizing the appropriate bis-iodo derivatives with various primary amines under similar conditions to those described by Calverley and Dale [31,32] (Scheme 7).…”

Section: Synthesis Of Monoaza-15-crown-5mentioning

confidence: 99%