铜（II）双恶唑啉配合物催化的恶唑烷介导的苯乙烯对映选择性氨羟基化反应。
Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes.
作者信息
Michaelis David J, Williamson Kevin S, Yoon Tehshik P
机构信息
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, WI 53706.
出版信息
Tetrahedron. 2009 Jun 27;65(26):5118-5124. doi: 10.1016/j.tet.2009.03.012.
Abstract
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.
摘要
我们报道了一种由手性铜（II）双恶唑啉配合物催化的、恶唑烷介导的烯烃对映选择性氨羟基化反应。多种苯乙烯类烯烃能高效地进行氨羟基化反应，具有出色的区域选择性和对映选择性（高达84% ee），对合成具有实用价值。该反应可以在多达数克的规模上进行，铜（II）催化剂的用量低至2 mol%。在酸性条件下，所得1,3-恶唑啉水解生成N-磺酰基氨基醇，可通过重结晶进行纯化，从而获得非常高的对映选择性。
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