Tetrahedron

Diastereoselective conjugate 1, 6-addition of lithium amides to naphthyloxazolines. Mechanistic studies and synthesis of δ-amino acid derivatives

M Shimano, A Matsuo

文献索引：Shimano, Masanao; Matsuo, Atsushi Tetrahedron, 1998 , vol. 54, # 19 p. 4787 - 4810

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被引用次数: 12

摘要

The novel 1, 6-amino addition reaction to the naphthalene ring system followed by the electrophilic alkylation is presented. The detailed mechanistic studies suggest the existence of two equilibrations that result in the 1, 4-amino addition reaction and the 1, 6-amino addition reaction. The stability and bulkiness of lithium amide play a key role in directing the course of the reaction. The transformation of the 1, 6-amino adducts to other useful ...