Enzymatic hydrolysis and synthesis of chrysanthemic acid esters

Sukumaran, Joly; Gool, Jacqueline van; Hanefeld, Ulf

doi:10.1016/j.enzmictec.2005.03.014

Cited by 9 publications

(4 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[23,24] Conversion of the enantiopure acetate to its TMS ether was performed according to a procedure from the literature. [25] Racemic cyanohydrin acetates were prepared by silylcyanation, deprotection and acylation according to the literature, [26][27][28] the spectroscopic data are in accordance with the literature: 1a [22] : General Procedure for the Enzymatic Hydrolysis [29,30] The cyanohydrin acetate 1a-d (1 mmol) was added to a 10 mM phosphate buffer at pH 7 (10 mL) and 25 8C. The enzyme (200 U) was added and the pH kept constant by the addition of a 0.1 M NaOH solution with an automatic burette.…”

Section: Experimental Section Materials and Methodsmentioning

confidence: 99%

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

et al. 2007

Self Cite

View full text Add to dashboard Cite

The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of a,a-disubstituted cyanohydrin acetates, a type of protected tertiary alcohols that form particularly interesting building blocks in organic synthesis. Utilising Subtilisin A the hydrolysis reaction was (S)-selective, while Candida rugosa lipase was (R)-selective. With these commercially available enzymes both enantiomers of the a,a-disubstituted cyanohydrin acetates are now accessible.

show abstract

Section: Experimental Section Materials and Methodsmentioning

confidence: 99%

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

et al. 2007

Self Cite

View full text Add to dashboard Cite

show abstract

“…In 2005, Sukumaran et al reported a hydrolytic lipase resolution applied to a diastereomeric mixture of two chrysanthemic acid ester racemates 72 and 73 . The presence of two stereocenters raised the possibility of achieving both diastereoselectivity and enantioselectivity in a single lipase resolution.…”

Section: Resolution Methods For the Synthesis Of Chiral Cyclopentenonesmentioning

confidence: 99%

Synthesis of Chiral Cyclopentenones

et al. 2016

View full text Add to dashboard Cite

The cyclopentenone unit is a very powerful synthon for the synthesis of a variety of bioactive target molecules. This is due to the broad diversity of chemical modifications available for the enone structural motif. In particular, chiral cyclopentenones are important precursors in the asymmetric synthesis of target chiral molecules. This Review provides an overview of reported methods for enantioselective and asymmetric syntheses of cyclopentenones, including chemical and enzymatic resolution, asymmetric synthesis via Pauson-Khand reaction, Nazarov cyclization and organocatalyzed reactions, asymmetric functionalization of the existing cyclopentenone unit, and functionalization of chiral building blocks.

show abstract

“…Vinyl chrysanthemates 1an, 1ao that have found application in enzymology, have been prepared in high yields from chrysanthemic acid by formal substitution reaction implying vinyl acetate catalyzed by palladium diacetate in basic media (Scheme 39, entry a) 108 or addition to ethoxyacetylene implying a ruthenium catalyst (Scheme 39, entry b). 108 Scheme 39. Synthesis of vinyl chrysanthemates from chrysanthemic acid.…”

Section: Alkylation Of Vinylcyclopropane Carboxylic Acids With Diazom...mentioning

confidence: 99%

Pyrethroid insecticides Chapter IVa. Reactivity of chrysanthemic acid and its lower esters

Krief¹

2022

Arkivoc

View full text Add to dashboard Cite

The reactivity of chrysanthemic acid and of its "lower esters" (methyl, ethyl, isopropyl and t-butyl) has played a crucial role in their structure elucidation, the discovery of new insecticides and in the understanding of their environmental fate.The reactivity of the carboxylic acid moiety and of its esters, that of the isobutenyl moiety and that of the cyclopropane ring are orthogonal to each other. The fact that this compound class is of relevance for industry has increased the diversity of the reactions disclosed especially that in the patented literature that associates science and economy and is at the roots of the green chemistry.

show abstract

Enzymatic hydrolysis and synthesis of chrysanthemic acid esters

Cited by 9 publications

References 26 publications

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

Hydrolase‐Catalysed Preparation of Chiral α,α‐Disubstituted Cyanohydrin Acetates

Synthesis of Chiral Cyclopentenones

Pyrethroid insecticides Chapter IVa. Reactivity of chrysanthemic acid and its lower esters

Contact Info

Product

Resources

About