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Stereoselectivity, malonic acid aldehydes

The alkylidene-1,3-dicarbonyl moiety is also a highly reactive enophile. Thus, the Knoevenagel adduct (223) obtained from aldehyde (222) and dimethyl malonate in the presence of piperidinium acetate, cy-clizes by treatment with Lewis acids such as FeCb on AI2O3 exclusively to the rranr-substituted cyclohexane (224 trans.cis > 99.5 0.5 Scheme 44).7 °3 The sesquiterpene veticadinol (225) has been synthesized in enantiomerically pure form by this method.Contrary to the expectation, rranr-sub-stituted cyclopentanes can also be obtained with excellent induced and noninduced dia-stereoselectivities. Similarly, aldehydes containing an allylsilane moiety can be used for a highly stereoselective formation of rran.r-l,2-disubstituted cyclopentanes and cyclohexanes by a Knoevenagel... [Pg.373]

See other pages where Stereoselectivity, malonic acid aldehydes is mentioned: [Pg.986]    [Pg.986]    [Pg.704]    [Pg.704]    [Pg.8]    [Pg.795]    [Pg.639]    [Pg.455]    [Pg.342]    [Pg.385]    [Pg.342]    [Pg.373]    [Pg.385]    [Pg.74]    [Pg.593]    [Pg.36]    [Pg.103]    [Pg.344]    [Pg.20]    [Pg.342]    [Pg.373]    [Pg.385]    [Pg.723]    [Pg.1352]    [Pg.723]    [Pg.1352]   
See also in sourсe #XX -- [ Pg.198 ]



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Aldehydes stereoselectivity

Malonates, acidity

Malonic acid

Malonic acid / Malonate

Malonic acid acidity

Malonic acid acids

Malonic aldehyde

Stereoselectivity acids

Stereoselectivity, malonic acid

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