Allen B. Reitz

Pyrrolidine and piperidine aminosugars from dicarbonyl sugars in one step. Concise synthesis of 1-deoxynojirimycin

Abstract Dicarbonyl sugars are convenient substrates for the stereoselective synthesis of hydroxylated piperidines and pyrrolidines, via a double reductive amination reaction (NaCNBH3, MeOH). Using this strategy, 2,5-anhydro-imino-D-glucitol (1) and 1-deoxynojirimycin (3) were prepared from 5-keto-D-fructose (2, commercially available) and 5-keto-D-glucose (4), respectively.

NMR rate study on the Wittig reaction of 2,2-dimethylpropanal and tributylbutylidenephosphorane

Abstract The fate of intermediate oxaphosphetanes in the reaction of t -BuCHO and Bu 3 Pue5fbCHPr was monitored with time. Cis oxaphosphetane 1a was converted to trans oxaphosphetane 1b at −55 °C with k 3 = 1.5 ⊚ 10 −4 s −1 , and 1b was converted to Bu 3 Pue5fbO and alkene 2b at −15 °C with k 6 = 2.7 ⊚ 10 −5 s −1 (t 1 2 = 7.0 h).