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Stereospecific formation of deuterated homoallyl alcohols by Lewis acid-promoted reactions of allyltin and allylsilicon reagents toward aldehydes

โœ Scribed by Yutaka Nishigaichi; Akio Takuwa

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
74 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 results strongly indicate both reactions proceed via a syn-synclinal transition state.

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