对映选择合成
化学
恶唑啉
区域选择性
催化作用
铜
恶嗪啶
有机化学
磺酰
水解
对映体药物
组合化学
烷基
作者
David J. Michaelis,Kevin S. Williamson,Tehshik P. Yoon
出处
期刊:Tetrahedron
[Elsevier]
日期:2009-03-10
卷期号:65 (26): 5118-5124
被引量:91
标识
DOI:10.1016/j.tet.2009.03.012
摘要
We report an oxaziridine-mediated enantioselective aminohydroxylation of olefins catalyzed by a chiral copper(II) bis(oxazoline) complex. A variety of styrenic olefins undergo efficient aminohydroxylation with excellent regioselectivity and synthetically useful levels of enantioselectivty (up to 84% ee). The reaction can be conducted on multi-gram scale with as little as 2 mol% of the copper(II) catalyst. Hydrolysis of the resulting 1,3-oxazolines under acidic conditions produces N-sulfonyl amino alcohols that can be purified by recrystallization to afford very high levels of enantioselectivity.
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