与邻位取代二芳基酮的催化对映选择性Reformatsky反应。

Catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones.

作者信息

Fernández-Ibáñez M Angeles, Maciá Beatriz, Minnaard Adriaan J, Feringa Ben L

机构信息

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

出版信息

Org Lett. 2008 Sep 18;10(18):4041-4. doi: 10.1021/ol801574m. Epub 2008 Aug 21.

DOI:10.1021/ol801574m

PMID:18715009

Abstract

The catalytic enantioselective Reformatsky reaction with ortho-substituted diarylketones with good enantioselectivities and moderate to good yields is reported. A readily available BINOL derivative is used as a chiral catalyst, and the reactions are performed with ethyl iodoacetate as a nucleophile and Me2Zn as the zinc source. The presence of air was found to be crucial to achieve an effective C-C bond formation pointing to a radical mechanism.

摘要

报道了与邻位取代二芳基酮的催化对映选择性Reformatsky反应，该反应具有良好的对映选择性和中等至良好的产率。一种易于获得的联萘酚衍生物用作手性催化剂，反应以碘乙酸乙酯作为亲核试剂，二甲基锌作为锌源进行。发现空气的存在对于实现有效的碳-碳键形成至关重要，这表明反应机理为自由基机理。