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2005
Pyran derivatives
R 0340
A Catalytic Asymmetric Bioorganic Route to Enantioenriched TetrahydroDihydropyranones. — A conceptually novel approach towards tetrahydro- and
25- 131 and
dihydropyranones is presented, involving an antibody-mediated kinetic resolution of
β-hydroxyenones (I) as key step. A diversity of β-hydroxyenones is tolerated as substrate, but those containing longer alkyl chains at the double bond are unreactive. This
drawback can be overcome by introduction of the alkyl chain by metathesis into enantiopure (Ia) after kinetic resolution [cf. (III)]. The enantioenriched β-hydroxyenones are
converted to the corresponding tetrahydrohydropyranones (IV) and (V) by TmsOTf-mediated cyclization or to dihydropyranone (VI) by Pd—Cu-catalyzed cyclization.
— (BAKER-GLENN, C.; HODNETT, N.; REITER, M.; ROPP, S.; ANCLIFF, R.;
GOUVERNEUR*, V.; J. Am. Chem. Soc. 127 (2005) 5, 1481-1486; Chem. Res.
Lab., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) — Mischke
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