Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.
Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.
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DOI：
10.1002/anie.200905000
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发表时间：
2010
影响因子：
16.6
通讯作者：
Toste, F. Dean
中科院分区：
文献类型：
--
作者：
LaLonde, R. L.;Wang, Z. J.;Mba, M.;Lackner, A. D.;Toste, F. Dean
金（I）催化的杂原子亲核试剂对联烯的加成[1]领域最近已扩展到包括杂环产物的对映选择性合成。[2，3]尽管这一研究领域的增长和含有多个杂原子的杂环的生物相关性，肼和羟胺亲核试剂对联烯的不对称加成尚未报道。[4]2007年，本课题组报道了金（I）-双对硝基苯甲酸配合物催化联烯的不对称氢胺化反应。[2a]我们假设，除了甲苯磺酰胺，金（I）-双-对-硝基苯甲酸配合物将作为有效的催化剂，对映选择性添加羟胺和肼的联烯。由这些反应形成的杂环，乙烯基异恶唑烷[5]和吡唑烷[6]经常出现在生物学上重要的分子中。[7]此外，这些杂环用作非天然氨基酸衍生物如5-氧杂脯氨酸[7，8]以及手性烯丙醇和1，3-二胺的前体。
The field of gold (I)-catalyzed addition of heteroatom nucleophiles to allenes [1] has recently expanded to include enantioselective synthesis of heterocyclic products.[2, 3] Despite the growth in this area of research and the biological relevance of heterocycles containing multiple heteroatoms, the asymmetric addition of hydrazine and hydroxylamine nucleophiles to allenes has not yet been reported.[4] In 2007, our group reported the enantioselective hydroamination of allenes catalyzed by gold (I)-bis-p-nitrobenzoate complexes.[2a] We hypothesized that in addition to tosyl amines, gold (I)-bis-p-nitrobenzoate complexes would perform as efficient catalysts for the enantioselective addition of hydroxylamines and hydrazines to allenes. The heterocycles formed from these reactions, vinyl isoxazolidines [5] and pyrazolidines,[6] appear frequently in biologically important molecules.[7] In addition, these heterocycles serve as precursors to unnatural amino acid derivatives such as 5-oxaproline [7, 8] as well as chiral allylic alcohols and 1, 3-diamines.
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影响因子：
56.9
作者：
Hamilton, Gregory L.;Kang, Eun Joo;Toste, F. Dean
通讯作者：
Toste, F. Dean
影响因子：
5.2
作者：
Kinder, Robert E.;Zhang, Zhibin;Widenhoefer, Ross A.
通讯作者：
Widenhoefer, Ross A.
影响因子：
16.6
作者：
Nishina, Naoko;Yamamoto, Yoshinori
通讯作者：
Yamamoto, Yoshinori
影响因子：
15
作者：
Buhrlage, SJ;Brennan, BB;Mapp, AK
通讯作者：
Mapp, AK
影响因子：
1.8
作者：
VASELLA, A;VOEFFRAY, R;HUGUENIN, R
通讯作者：
HUGUENIN, R