Tetrahedron p. 749 - 758 (1994)
Update date:2022-08-02
Topics: Stereochemistry applications Reaction Components Convenience Reaction Mechanism
Binder, Wolfgang H.
Prenner, Reinhard H.
Schmid, Walther
The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity.Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated.The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
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