The above bicyclic lactone can be synthesized by phase transfer catalysis or in DMSO under ultrasonic activation. Alkylation with epihalohydrines of anionic species generated from phenylacetonitrile or alkyl phenylacetate is followed by possible hydrolysis and further cyclization in acidic medium. (C) Academie des sciences/Elsevier, Paris.

A new methodology leading to ketene O,O- and S,S-acetals is reported. The title compounds were prepared from the corresponding halogenated precursors under microwave irradiation in the absence of solvent within 5–25 minutes with excellent yields. Yields obtained under microwaves are by far the best when compared to those obtained by ultrasound or classical heating in the same conditions of time and temperature.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Alpha-n-amylcinnamaldehyde (jasminaldehyde) was obtained with 82 % yield by solid-liquid phase transfer catalysis without solvent within 3 days at room temperature. By use of domestic microwave irradiation, the same yield was obtained within 1 minute at a power of 600 W.

Alkylation of 1,2,4-triazole and benzotriazole has been performed either in basic media under solvent free phase transfer catalysis conditions or in the absence of base by conventional and microwave heating. Several parameters affecting the selectivity have been studied. In the case of triazole alkylation, microwave irradiation produces specific (non thermal) effects both on reactivity and selectivity.

A fatty epoxide (tetradecyl-oxirane) is reacted with diethyl acetamidomalonate in basic medium, with or without solvent under solid-liquid phase transfer catalysis with LiCl, or under microwave irradiation on supported reagents (KF/Al2O3/LiCl). The main product is a lactone which is formed after epoxide ring opening and subsequent cyclisation. We put here into evidence, for the first time, the conjugated advantages of ''dry media'' reactions, lithium salt effects and microwave irradiation.

Cyano-[D11]-cyclohexane was prepared from commercial [D12]-cyclohexanol via the sequence alcohol-chloride-acid-nitrile in an overall yield of 33 % after purification. Isotopic purity was at least 98 %.

AbstractHigh stereoselectivity is observed for the addition of sterically demanding organozinc reagents derived from the Grignard compounds (II).

Organozinc compounds readily obtained in situ from Grignard reagents and solutions of ZnCl2 or ZnBr2 in diethylether or THF add selectively to the keto group of (−) menthyl phenylglyoxalate. A variety of α-substituted mandelic acids of known absolute configurations were obtained in high yields by this route, with in most cases high levels of enantiomeric excess.

AbstractThe chiral phenylglyoxalate (I) reacts with dialkylzinc compounds which are prepared in situ from zinc chloride and the Grignard compounds (II) to form the hydroxy esters (III).

Organozinc compounds (from Grignard reagents and ZnCl2 or ZnBr2 in diethylether of THF) add selectively to the keto group of (−) menthyl phenylglyoxalate, to give α-substituted (−) menthyl mandelates in high yields and in most cases high levels of asymmetric induction.

Chemischer InformationsdienstVolume 17, Issue 4 Isocyclic Compounds ChemInform Abstract: Application of Hydro-Alumination-Reactions to Organic Synthesis. G. BOIREAU, G. BOIREAUSearch for more papers by this authorA. KORENOVA, A. KORENOVASearch for more papers by this authorA. DEBERLY, A. DEBERLYSearch for more papers by this authorD. ABENHAIM, D. ABENHAIMSearch for more papers by this author G. BOIREAU, G. BOIREAUSearch for more papers by this authorA. KORENOVA, A. KORENOVASearch for more papers by this authorA. DEBERLY, A. DEBERLYSearch for more papers by this authorD. ABENHAIM, D. ABENHAIMSearch for more papers by this author First published: January 28, 1986 https://doi.org/10.1002/chin.198604135Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume17, Issue4January 28, 1986 RelatedInformation

Using tetraalkylaluminates prepared via hydroalumination in THF of various vinyl compounds resulted in selective addition to the keto group of phenylglyoxylic acid (−) menthyl ester. Not only simple alkyl groups but also functionalized alkyl groups were added. By this way, a variety of α-substituted mandelic acid (−) menthyl esters were obtained with diastereomeric excesses close to 70%.

Using tetraalkylaluminates prepared via hydroalumination in THF of various vinyl compounds resulted in selective addition to the keto group of phenylglyoxylic acid (−) menthyl ester. Not only simple alkyl groups but also functionalized alkyl groups were added. By this way, a variety of α-substituted mandelic acid (−) menthyl esters were obtained with diastereomeric excesses close to 70%.

AbstractDas aus äquimolaren Mengen iBu3Al und dem Li‐Salz des (+)‐Darvonalkohols hergestellte chirale Reagens (IIa) reagiert in Hexan mit dem α‐Ketoester (I) zum α‐Hydroxyester (IIIa), aus dem durch Hydrolyse die (2S)‐kon?guierte Hydroxysäure (IVa) in einer optischen Reinheit von 85% e.e.

Chemischer InformationsdienstVolume 15, Issue 23 Isocyclic Compounds ChemInform Abstract: HIGH OPTICAL YIELD IN SYNTHESIS OF α-ALKYL-α-HYDROXY ESTERS BY REACTION OF BULKY ALKOXYTRIALKYLALUMINATES WITH MENTHYL PHENYLGLYOXALATE A. DEBERLY, A. DEBERLYSearch for more papers by this authorG. BOIREAU, G. BOIREAUSearch for more papers by this authorD. ABENHAIM, D. ABENHAIMSearch for more papers by this author A. DEBERLY, A. DEBERLYSearch for more papers by this authorG. BOIREAU, G. BOIREAUSearch for more papers by this authorD. ABENHAIM, D. ABENHAIMSearch for more papers by this author First published: June 5, 1984 https://doi.org/10.1002/chin.198423188Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume15, Issue23June 5, 1984 RelatedInformation

Enantiomeric purities in alkylation of (+) and (−) menthyl esters of phenylglyoxilic acid by complexes derived from AlEt3 and the lithium salts of (+) and racemic Darvon alcohol are depending upon the only stereochemistry of the menthyl group in ester. These results suggest that the observed stereoselectivity is to be related to the bulkiness of the organometallic reagent, which overcomes the asymetric induction due to the chiral center of the alkoxy moiety. Accordingly, use of complexes from AlEt3 and non chiral alcohols of increasing sizes leads to increasing stereoselectivity.

Enantiomeric purities in alkylation of (+) and (−) menthyl esters of phenylglyoxilic acid by complexes derived from AlEt 3 and the lithium salts of (+) and racemic Darvon alcohol are depending upon the only stereochemistry of the menthyl group in ester. These results suggest that the observed stereoselectivity is to be related to the bulkiness of the organometallic reagent, which overcomes the asymetric induction due to the chiral center of the alkoxy moiety. Accordingly, use of complexes from AlEt 3 and non chiral alcohols of increasing sizes leads to increasing stereoselectivity.

AbstractPhenylglyoxylsäure+)‐menthylester (I) reagiert mit den Organoaluminiumverbindungen (II), deren Herste1lung beschrieben ist, zu den Hydroxy‐carbonsäureestern (III) bzw. den freien Säuren (IV) in hohen optischen Ausbeuten.

The reaction of chiral MAIR3OR* (M = Li, Na, K ; R = Me, Et ; OR* from R*OH = (−)N-methylephedrine) with C6H5COCO2 (−)-menthyl provide a good synthesis of α-alkyl mandelic acids with enantiomeric excess (e.e.) up to 53%. Asymmetric induction due to both the chiral centers of the (−)-menthyl group and the OR* group may be invoked to account for the higher stereoselectivity observed in the reaction.