Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction
Synthesis of new tridentate chiral aminoalcohols by a multicomponent reaction and their evaluation as ligands for catalytic asymmetric Strecker reaction
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DOI：
10.1016/j.tet.2007.06.047
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发表时间：
2007-09-03
期刊：
影响因子：
2.1
通讯作者：
Vilaivan, Tirayut
中科院分区：
文献类型：
--
作者：
Banphavichit, Vorawit;Bhanthumnavin, Worawan;Vilaivan, Tirayut
苯酚、多聚甲醛和β-氨基醇在氯化锂存在下的一步多组分Mannich反应高邻位选择性地合成了N-2-羟基苄基恶唑烷。水解或还原开环的恶唑烷提供了一系列的N-水杨基-β-氨基醇，总收率为84-92%。合成的化合物作为钛催化的催化不对称Strecker反应的配体进行了评价。使用10 mol %催化剂的反应以优异的产率和高达98%ee提供Strecker产物。（c）2007 Elsevier Ltd.保留所有权利。
A one-step, multicomponent Mannich-type reaction between phenols, paraformaldehyde, and beta-aminoalcohols in the presence of LiCl afforded N-2-hydroxybenzyloxazolidines with high ortho-selectivity. Hydrolytic or reductive ring opening of the oxazolidines provided a series of N-salicyl-beta-aminoalcohols in 84-92% overall yield. The synthesized compounds were evaluated as ligands for a titanium-catalyzed catalytic asymmetric Strecker reaction. The reaction employing 10 mol % of catalyst provided the Strecker products in excellent yields and up to 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.