Dimethyl Sulfoxide → (1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

Participants

Reaction Steps

(S)-Cyclohex-3-enecarboxylic acid (1.98 g, 15.7 mmol) ([α]D=−92.7° (c=1, CHCl3)=97.5% e.e., resolved by the method of Schwartz et al, J. Am. Chem. Soc., 100, 5199, (1978)) was reacted with trimethylsilyl bromide (4.10 mL, 31.3 mmol), DMSO (2.23 mL, 31.3 mmol), and N,N-diisopropylethylamine (4.45 mL, 31.3 mmol) (by a modification of the method of Iwata et al, Heterocycles., 31, 987 (1990)) to give a white solid, (2.91 g, 14.2 mmol, 90%);

Provenance & Evidence