期刊
PURE AND APPLIED CHEMISTRY
卷 78, 期 7, 页码 1397-1406出版社
WALTER DE GRUYTER GMBH
DOI: 10.1351/pac200678071397
关键词
chiral homoallylic amines; N-substituted imines; allylboron reagents; organoboranes; homoallylic amines; N-aluminoimines
Among the plethora of protocols for the preparation of chiral homoallylic amines, the use of boron-based reagents remains relatively undeveloped. However, the recent advances in the use of alpha-pinene-based versatile reagents for the synthesis of such amines confirmed that very high enantioselectivity and outstanding diastereoselectivity can be readily achieved. Addition of the allylboron reagents to various N-substituted imines provided the desired amine products in high yields and high to very high ee. The discovery that an addition of 1.0 equiv of methanol or water to the allylboration reaction with N-masked imines is critical allowed for higher yields and noticeably improved ee. The use of N-aluminoimines, which are not only easy to prepare by a partial reduction of nitriles, but are also relatively stable for both enolizable and non-enolizable substrates, considerably expanded the scope of the reactions. In this review, the developments in the syntheses of chiral homoallylic amines using organoboranes, with the particular accent on the reagent-controlled reactions, are summarized. Additionally, the novel methodology for the crotyl- and alkoxyallylboration of imines using trialkylboron ate complexes is described.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据