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Reversible stereocontrol in the Lewis acid promoted reaction of alkoxyaldehydes toward various allyltins

โœ Scribed by Yutaka Nishigaichi; Akio Takuwa

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
175 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 exceptional. This reversible diastereoselectivity can be explained by the coordination geometry (anti or syn) of the Lewis acids toward alkoxyaldehydes.

๐Ÿ“œ SIMILAR VOLUMES

Stereospecificity in the Lewis acid prom
Stereospecificity in the Lewis acid promoted allylation reaction of 3,3-disubstituted allyltins toward aldehydes
โœ Yutaka Nishigaichi; Akio Takuwa ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 217 KB

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

Stereospecific formation of deuterated h
Stereospecific formation of deuterated homoallyl alcohols by Lewis acid-promoted reactions of allyltin and allylsilicon reagents toward aldehydes
โœ Yutaka Nishigaichi; Akio Takuwa ๐Ÿ“‚ Article ๐Ÿ“… 2002 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 74 KB

Stereoselectively prepared (Z)-3-deuterioallyltin and (E)-3-deuterioallylsilicon were allowed to react with aldehydes in the presence of BF 3 โ€ขOEt 2 . The stereospecifically afforded products were predominantly an anti-homoallyl alcohol from the (Z)-reagent and a syn-one from the (E)-reagent. These