State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
J Am Chem Soc. 2014 Feb 5;136(5):1766-9. doi: 10.1021/ja412023b. Epub 2014 Jan 23.
A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.
发展了一种钯催化的烯烃分子内氨羟化反应，其中 H2O2 被用作唯一的氧化剂。通过 H2O2 对烷基 C-Pd 键的氧化裂解，可以以良好的收率和优异的非对映选择性得到多种相关的烷基醇。这些产物的易于转化为合成 2-氨基-1,3-二醇和 3-醇氨基酸提供了有力的工具。初步的机理研究表明，高价钯中心的水（S(N)2 型）的主要亲核进攻有助于最终的 C-O(H)键形成。
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