叔丁基亚磺酰基异氰酸酯在碱性条件下的 Aldol 反应用于反式 Aldols 的非对映选择性合成。
Aldol Reaction of N-tert-Butanesulfinyl Imidates under Basic Conditions for Diastereoselective Synthesis of anti-Aldols.
机构信息
Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences , Urumqi 830011, China.
University of the Chinese Academy of Sciences , Beijing 100049, China.
出版信息
J Org Chem. 2017 Oct 20;82(20):11253-11261. doi: 10.1021/acs.joc.7b01982. Epub 2017 Sep 28.
Diastereoselective aldol reaction of N-tert-butanesulfinyl imidates under typical hard enolization conditions is reported. Potassium bis(trimethylsilyl)amide (KHMDS) effectively promotes the aldol reaction of α-aryl- and α-alkyl-substituted imidates, providing anti-aldol adducts in high yields with good to excellent diastereoselectivities. In the case of α-aryl imidates, high conversion depends on adding trimethylsilyl chloride (TMSCl) to the reaction mixture. In the presence of a suitable Lewis acid, cyclohexanone is a good electrophile in the aldol reaction of imidates.
本文报道了在典型的硬烯醇化条件下 N-叔丁基亚磺酰基异氰酸酯的非对映选择性羟醛缩合反应。双(三甲基甲硅烷基)酰胺钾（KHMDS）有效地促进了α-芳基和α-烷基取代异氰酸酯的羟醛缩合反应，以高收率和优异至极好的非对映选择性提供了反式羟醛缩合产物。在α-芳基异氰酸酯的情况下，高转化率取决于向反应混合物中添加三甲基氯硅烷（TMSCl）。在合适的路易斯酸存在下，环己酮是异氰酸酯的羟醛缩合反应的良好亲电试剂。
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