Electrophilic heterocyclization of unsaturated carboxylic acids in the synthesis of lactones (review)

Gevaza, Yu. I.; Станинец, В. И.

doi:10.1007/bf00475678

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Cited by 5 publications

(1 citation statement)

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“…12, 14 Hence, we extended the reaction to monomethyl ester 9 (obtained by esterification of potassium salt of the diacid 7 with methyl iodide in HMPT-THF (1:2) and obtained lactone 10, in 52% yield, together with hydroxyl-acid lactone 8 in 26% yield; thus lactonization is realized in almost the same overall isolated yield (88%) as for diacid 7. This was expected due to the fact that diacid 7, synthesized from endo-DCPD, (and monoester 9 as a consequence), is a mixture of two isomers with the double bond at C 4 or C 5 atoms.…”

Section: Chemistrymentioning

confidence: 92%

Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton

Tănase

Drăghici²,

Shova³

et al. 2015

Tetrahedron

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Section: Chemistrymentioning

confidence: 92%

Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton

Tănase

Drăghici²,

Shova³

et al. 2015

Tetrahedron

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Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids

et al. 2016

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At wo-step( nucleophilic substitution/palladation by oxidative addition) sequence provides ah igh-yielding access to an on-symmetrical palladium NNC pincerc omplex. An umber of terminal and internal alkynoic acids with different substitution patternsa tt he a-a nd b-positions are regioand diastereoselectively cycloisomerizedt ot he corresponding exocyclic enol lactones in the presence of exceedingly low amounts of the latter palladium complex, so that unprecedented turnovern umbers and frequencies ranging from 1,000,000 to 700,000 and from 41,667 to 9722h À1 ,r espectively, are achieved. Theo ptimized protocol, based on the use of ac atalytic amount of triethylamine as base,a llows an easy real-time monitoring of the reactionb y NMR spectroscopy.S everal pieces of evidence in favor of the direct participation of the above pincer complex as the catalyst of the reaction have been gathered from kinetic and poisoning experiments

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Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII

et al. 2009

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Electrophilic heterocyclization of unsaturated carboxylic acids in the synthesis of lactones (review)

Cited by 5 publications

References 180 publications

Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton

Regioselective reactions on a 1,3-disubstituted dihydroxymethyl or dicarboxyl hexahydropentalene skeleton

Palladium NNC Pincer Complex as an Efficient Catalyst for the Cycloisomerization of Alkynoic Acids

Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between AuI and AuIII

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