Highly efficient synthesis of alkyl pyrrolylacetates and dialkyl pyrrolylmalonates

…, R Greenhouse, JM Muchowski

文献索引：Schloemer, George C.; Greenhouse, Robert; Muchowski, Joseph M. Journal of Organic Chemistry, 1994 , vol. 59, # 18 p. 5230 - 5234

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被引用次数: 19

摘要

N-Pyrrolylmagnesium halides (1, 2) react with alkyl bromoacetates (sa-d) in THF solution to give alkyl 2-pyrrolylacetates (sa-d) in good yields and with very high positional selectivity (C- 2: C-3 t 25). The high regioselectivity is rationalized in terms of an increased propinquity between C-2 and the bromoacetate methylene group as a consequence of coordination between magnesium and the carbonyl oxygen of the alkylating agent.(2, 5-Dimethylpyrrol- ...