Synthesis of Arylpropylamines . I . From Allyl Chloride 1
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Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols.
A highly regio- and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-alpha,beta-d-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-beta-acetates or -carbonates in excellent yields. The 2-OH, 1-beta-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl tr...
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The Claisen rearrangement and its applications to organic synthesis have been studied for a long time.l In recent years, this rearrangement has been applied in stereocontrolled natural product synthesis2 and asymmetric i n d ~ c t i o n . ~ The term "Claisen rearrangement", which originally denoted the rearrangement of allyl aryl ethers to 0or p-allylphenols, has now been extended to analogous ...
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A one-pot, convenient method for the preparation of optically active homoallylic alcohols from allyl halides was developed. Allyltrichlorosilanes were generated in situ from allyl halides and trichlorosilane in the presence of cuprous chloride and tertiary amine. Without isolation of the allyltrichlorosilanes, benzaldehyde and chiral biquinoline N,N'-dioxide were introduced into the same flask,...
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Homoallylic ketones combine arguably two of the most synthetically useful functional groups in organic chemistry and are, therefore, very valuable synthetic intermediates. General methods for the synthesis of these intermediates include the allylation of carbonyl compounds via p-allyl palladium(II) complexes, the 1,4-addition of vinylmetal nucleophiles onto a,bunsaturated compounds, and the Cla...
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تاریخ انتشار 2008