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Homophthalic anhydride ( 1 ) reacts with wide variety of aromatic aldehydes, in the presence of chloroform and DMAP ( N , N -dimethyl-4-amino-pyridine) at room temperature, to give in high yields cis - and trans -1-oxo-isochroman-4-carboxylic acids. Under these conditions, the trans -isomer is...
Three different methods are reported for the preparation of 4-azacyclo-2-enones 1 , two of which allow the preparation of the compounds in optically active form. In addition, a facile route to 4-aza-5,5-dimethylcyclopent-2-enones 2 is disclosed.
Non-epimerizable cis and trans δ-lactone analogues of podophyllotoxin have been prepared. Thus the synthesis of the cis isomer 4 has been achieved in 8 steps and 4% overall yield from podophyllotoxin 1 via the reduction of the γ lactone ring into the trans diol, selective protection of the 4-OH...
A protocol has been established for the transformation of chiral ortho 1-hydroxyethyl propenyl benzenes under both anaerobic and oxidative mercury(II) mediated conditions to produce chiral isochromanes. Further transformations of the former products yielded chiral isochromanquinones, while the...
N -Vinylic phosphazenes react as enamines (1,4-addition) with azodicarboxylic esters, whereas different behavior is observed when these phosphazenes react with dimethyl acetylenedicarboxylate (3,4-addition). A (2+2) cycloaddition reaction of the vinyl moiety of vinylic phosphazenes with the...
The Pauson–Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo(3.3.0)octenone and bicyclo(4.3.0)nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to...
The rhodium (I) catalysed tandem hydrosilylation-intramolecular aldol reaction provides a simple strategy for construction of a range of usefully functionalised five-membered rings from readily prepared 6-oxo-2-hexenoates in good yield and with good to excellent stereoselectivity. A series of...
Silyl-assisted elimination reaction of glucopyranosyl carbamates has been established for the synthesis of α- and β- d -glucopyranosyl isocyanates and ureas. This method proved to be useful for the synthesis of urea-tethered neoglycoconjugates.
On the basis of competition experiments using a model VNS reaction of chloromethyl phenyl sulfone with halonitrobenzenes it was shown that halogen substituents activate electron-deficient nitroarenes for the addition of carbanions whereas they protect the positions they occupy against the addition.
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