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TFA-catalyzed trimerization of R-(+)-6-methyl-tetrahydro-pyran-2-one

✍ Scribed by Fabio Fazio; Manfred P. Schneider

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

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✦ Synopsis

The enantiomerically pure (]98% ee) title compound R-(+)-6-methyl-tetrahydro-pyran-2-one (R)-1 in the presence of traces of trifluoroacetic acid (TFA) converts into an equilibrium mixture with its trimer 4 [(R)-1:4=20:80] corresponding to a DG$-0.8 kcal mol -1 . The transformation can be followed by 1 H and 13 C NMR spectroscopy. The structure of 4 was established by chemical correlation with (R)-1 and its molecular weight determined via its colligative properties.

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