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

Participants

Reaction Steps

(R)-Cyclohex-3-enecarboxylic acid, 98.2% e.e, (2.30 g, 18.2 mmol) [Schwartz et al, J. Am. Chem. Soc., 100, 5199, (1978)] was reacted with trimethylsilyl bromide (3.01 mL, 22.8 mmol), DMSO (1.62 mL) and N,N-diisopropylethylamine (3.97 mL, 22.8 mmol) [by the method of Iwata et al, Heterocycles., 31, 987 (1990)] to give a white solid, (2.13 g, 57%).

Provenance & Evidence