Chapuis, Christian; Buchi, George H.; Wuest, Hans published their research in Helvetica Chimica Acta on December 23 ,2005. The article was titled 《Synthesis of cis-Hedione and methyl jasmonate via cascade Baylis-Hillman reaction and Claisen ortho ester rearrangement》.Product Details of 329735-68-4 The article contains the following contents:
The exocyclically unsaturated conjugated keto esters I (R = n-Bu, n-hexyl, PhCH2OCH2, etc., R1 = Me, Et), obtained via a Claisen ortho ester rearrangement of the allylic hydroxy ketones II, were either directly hydrogenated or partially isomerized into the endocyclically unsaturated tetrasubstituted didehydrojasmonoid intermediates III, prior to a more selective hydrogenation with Pd/C in cyclohexane to the disubstituted oxocyclopentaneacetates IV. The key intermediates II were obtained either by a four-step sequence, including acetal protection/deprotection from enone V, in the specific case of hydroxy ketone II (R = n-Bu), or more directly and generally by a Baylis-Hillman reaction from cyclopent-2-en-1-one and the appropriate aldehydes RCHO. The judicious choice of these aldehydes opens versatile modifications for the stereoselective introduction of the partially cis- or epimerized trans-C(2) jasmonoid side chain, while the Baylis-Hillman reaction, catalyzed by chiral [1,1′-binaphthalene]-2,2′-diols (BINOLs), may be efficiently conducted in a one-pot cascade fashion including the ortho ester Claisen rearrangement.(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Product Details of 329735-68-4) was used in this study.
(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Product Details of 329735-68-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts