Allyl bromide → (2S,3R)-3-allyl-1-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 47 (0.200 g, 0.823 mmol) in THF (5 ml) at −78° C. was added a solution of LDA (1.10 ml, 2.4 eq.). The reaction solution was stirred for 20 min. at that temperature, warmed to −20° C. and allyl bromide (0.138 Ml, 2.0 eq.) was added slowly. Reaction mixture was warmed to 0° C. for 30 min. and quenched with KHSO4 (20 ml, 10%), extracted with ethyl acetate (3×). Combined organic layers were washed with brine twice and dried over MgSO4. After concentrating in vacuo, compound 48 was obtained. H1NMR (CDCl3): 0.15, 0.37 (s, 6H), 1.16 (s, 9H), 1.33 (s, 3H), 2.50 (m, 2H), 3.98 (s, 1H), 5.22 (m, 2H), 5.88 (m, 1H). C14H25NO3Si, Mol. Wt.: 283.44. Found: 284 (M+1).

Provenance & Evidence