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Stereochemically divergent pathways for the allylation and crotylation reactions of anti- and syn-β-hydroxy-α-methyl aldehydes with allyl- and crotyltrifluorosilanes

✍ Scribed by Sherry R. Chemler; William R. Roush

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

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✦ Synopsis

Allylation and crotylation reactions of 2,3-anti-B-hydroxy-a-methyl aldehydes 10 and 11 with ally1 and crotyltrifluorosilanes 2, 8 and 9 proceed with high selectivity via the bicyclic chelated transition states 3 and 30. In contrast, analogous allylation and crotylation reactions of the 2,3-syn-l3-hydroxy-(x-methyl aldehydes 12 and 13 with 2,s and 9 are generally less selective and proceed preferentially by way of the normal Zimmerman-Traxler transition states 6 and 32.

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