Methyl morpholine oxide → (4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-one

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Reaction Steps

Tetrapropylammonium perruthenate (9.4 mg, 0.027 mmol) was added to a mixture of (1S,4R)-4-(tert-butyldimethylsilanyloxy)cyclopent-2-enol prepared, according to Tetrahedron Letters, Vol. 37, No. 18, 1996, pp. 3083-6, (118.6 mg, 0.54 mmol), 4-methylmorpholine N-oxide (94.9 mg, 0.81 mmol) and crushed 4 Å sieves (270 mg) in CH2Cl2 (10 mL). The mixture was stirred for 30 min and was passed through a plug of silica gel with CH2Cl2. The filtrate was concentrated in vacuo to give 100 mg (86%) of the above titled compound.

Provenance & Evidence