Department of Chemistry, University of Maragheh , Maragheh 55181-83111, Iran.
Department of Chemistry, Payame Noor University , Tehran 19395-3697, Iran.
Chem Rev. 2017 Jun 28;117(12):8326-8419. doi: 10.1021/acs.chemrev.7b00064. Epub 2017 Jun 12.
α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.
α-亚氨基酯是合成各种天然和非天然α-氨基酸衍生物的有用前体,具有广泛的生物活性。由于相邻的酯基,α-亚氨基酯相对于其他类型的亚胺更具反应性,并经历不同类型的反应,包括有机金属加成、金属催化的乙烯基化和炔基化、氮杂-Henry、氮杂-Morita-Baylis-Hillman、亚氨基-烯、Mannich 型和环加成反应,以及加氢和还原。本综述讨论了α-亚氨基酯和相关化合物在有机合成中的反应的机制、范围和应用,涵盖了过去 12 年的文献。