Kumar Varun, Klimovica Kristine, Rasina Dace, Jirgensons Aigars
Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, Latvia LV 1006.
J Org Chem. 2015 Jun 5;80(11):5934-43. doi: 10.1021/acs.joc.5b00529. Epub 2015 May 18.
A diastereoselective synthesis of 4-vinyl oxazolines syn-2 was developed based on an acid-catalyzed cyclization of bistrichloroacetimidates (E)-1. The reaction likely involves an allyl carbenium ion intermediate in which the adjacent stereocenter directs the stereoselectivity for C-N bond formation. Oxazolines syn-2 were transformed to C-quaternary threoninol, threoninal, and threonine derivatives which can be further incorporated into complex natural compounds.
基于双（三氯乙酰亚胺酯）（E）-1的酸催化环化反应，开发了一种4-乙烯基恶唑啉syn-2的非对映选择性合成方法。该反应可能涉及烯丙基碳正离子中间体，其中相邻的立体中心指导C-N键形成的立体选择性。恶唑啉syn-2被转化为C-季碳苏氨醇、苏氨醛和苏氨酸衍生物，这些衍生物可进一步并入复杂的天然化合物中。
