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ChemInform Abstract: 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
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

1999 stereochemistry stereochemistry (general, optical resolution) O 0030 34 -040 Stereochemically Divergent Pathways for the Allylation and Crotylation Reactions of anti-and syn-β-Hydroxy-α-methyl Aldehydes with Allyl-and Crotyltrifluorosilanes. -Allylation of 2,3-anti-βhydroxy-α-methyl aldehydes [cf. (I)] with the trifluorosilane (II) proceeds with high diastereoselectivity via a bicyclic chelated transition state whereas the corresponding 2,3-syn-β-hydroxy-α-methyl aldehyde (V) reacts by the way of the normal Zimmerman-Traxler transition state in generally less selectivity. -(CHEMLER,

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