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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...
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...
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...
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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