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Stereospecificity in the Lewis acid promoted allylation reaction of 3,3-disubstituted allyltins toward aldehydes

โœ Scribed by Yutaka Nishigaichi; Akio Takuwa

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
217 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The Lewis acid-promoted reaction of 3,3-disul3stituted allyltins toward aldehydes was found to be stefeospecific; the (E)-reagent gave syn-products and the (Z)-one gave anti-products. This is in contrast to that of 3-mono-su~tituted congeners which are known to react syn-stereoselectively regardless of their double bond geometry. The reaction was assumed to proceed via an acyclic syn-synclinal transition state.

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In the reactions of variously substituted allyltin reagents toward achiral alkoxyaldehydes, one of the diastereomeric homoallyl alcohols was stereoselectively obtained by the help of BF 3 , while TiCl 4 preferentially gave the other diastereomer, though (E)-and (Z)-3-monoalkylallyltin reagents were