关键词:
3-bromopropenyl methylcarbonate
indium
oxidative addition
organoindium
5-vinyl-1,3-dioxolan-2-ones
摘要:
The reaction of 3-bromopropenyl methylcarbonate (2) with aliphatic or aromatic aldehydes, in the presence of indium metal in N,N-dimethylformamide, affords cis and trans 4,5-disubstituted 5 -vinyl-1,3-dioxolan-2-ones 4 in very high isolated yields. Reactions may be run by adopting either one-pot Barbier conditions or a two-step Grignard protocol, The cis-4/trans-4 ratio is controlled by the nature of the carbonyl compound: saturated aldehydes mainly afford cis-4, whereas conjugated aldehydes favor the formation of trans-4. (c) Wiley-VCH Verlag GmbH & Co.