Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydes

Drewes, Siegfried E.; Roos, Gregory

doi:10.1016/s0040-4020(01)86168-8

Cited by 689 publications

(168 citation statements)

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“…containing a minimum of three functional groups (hydroxy group, alkene, and electron withdrawing group) and one chiral center. [40][41][42][43] We have employed pig liver acetone powder (PLAP) for the enzymatic hydrolysis of acetates of the racemic Baylis-Hillman adducts (alcohols) to provide the corresponding optically active alcohols in 46-86% enantioselectivities and in 19-37% isolated yields 33 (Schemes 5 & 6).…”

Section: Methodsmentioning

confidence: 99%

Applications of liver acetone powders in enantioselective synthesis

Basavaiah¹

2001

Arkivoc

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Applications of liver acetone powders (crude enzymes) as possible substitutes for purified enzyme preparations, hydrolases, in enantioselective organic transformations have been systematically investigated. (1R, 2R)-2-(4-Alkylphenoxy)cyclohexan-1-ols, (1R, 2R)-& (1S, 2S)-2-nitroxycyclohexan-1-ols, (1R, 2S)-2-arylcyclohexan-1-ols, (3R, 4R)-6-methyl-3-phenylhept-1-en-4-ol, and (R)-1-(naphth-1-yl)ethanol have been synthesized in enantiomerically pure form via the enantioselective hydrolysis of the corresponding racemic acetates mediated by liver acetone powders.

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Section: Methodsmentioning

confidence: 99%

Applications of liver acetone powders in enantioselective synthesis

Basavaiah¹

2001

Arkivoc

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“…In this contest by considering nitromethylenyl imidazole group as essential for insecticidal activity we aimed to replace the nicotinyl heterocyclic ring with some Baylis-Hillman derived cinnamyl substituted compounds to findits potentiality as insecticides. The Baylis-Hillman reaction [25][26][27][28][29] has attracted the attention of organic chemists as this reaction provides synthetically useful multifunctional molecules. The develolpment of resistance to imidacloprid by pest insects is a significant concernand therefore, it is an ongoing effort to synthesize new insecticidal agents.…”

Section: Fig 1: Commercialized Neonicotinoid Insecticides and Activementioning

confidence: 99%

Untitled

2015

IJPSR

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ABSTRACT:A series of Baylis-Hillman derived N-cinnamyl substituted nitro methylene imidazole derivatives 4a-swere synthesizedfrom BaylisHillman acetates and nitro methylene imidazole compoundsand characterised by 1 H NMR, IR, Mass and HRMS spectroscopy. Their insecticidal activities were evaluated against T. Castaneum and compared with a standard insecticide Permethrane. Preliminary biological activity tests showed that most of the compounds exhibited good insecticidal activity against T. Castaneum at 100µg/cm 2 especially compounds 4b, 4g, 4i, 4l, 4n and 4r showed good insecticidal activity against T. castaneum, interestingly compound 4b with p-fluoro substitution displayed 75% activity. The structure-activity relationship showed that compounds with electron-with drawing substitutions like -F, -Br, -Cl, -NO 2 , -CF 3 at the para position havinggood insecticidal activity and compounds with electron-with drawing groups like -F, -Br at the meta position have shown moderate activity.This work provides some hints for further structural modifications on the Baylis-Hillman derivatives and the enhancement of insecticidal activity.

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“…4 In 1983, the reaction was rediscovered, and its scope was explored primarily by Drewes and Basavaiah. 5 Since then, alkyl vinyl ketones, acrylonitriles, vinyl sulfones, acrylamides, allenic esters, vinyl sulfonates, vinyl sulfoxides, vinyl phosphonates, and acroleins have been substituted 1 Versatile functionality, i.e. hydroxyl (or amino), alkene, and electron-withdrawing groups, make Baylis-Hillman adducts valuable intermediates in Friedel-Crafts [6][7][8] and Heck reactions, 9,10 hydride addition, 11,12 hydrogenation, [13][14][15][16] aminohydroxylation, 17 radical 18,19 and photochemical reactions 20 and 1,3-dipolar cycloaddition.…”

Section: 2mentioning

confidence: 99%