Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.
Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.
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DOI：
10.1021/jo500050n
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发表时间：
2014-03-21
期刊：
影响因子：
--
通讯作者：
Shaw JT
中科院分区：
文献类型：
--
作者：
Sorto NA;Di Maso MJ;Muñoz MA;Dougherty RJ;Fettinger JC;Shaw JT
Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.
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