手性叔丁基亚磺酰亚胺的锂化炔酰胺的高对映选择性加成。
A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States.
出版信息
Org Lett. 2013 May 17;15(10):2514-7. doi: 10.1021/ol400989x. Epub 2013 May 6.
Abstract
A highly diastereoselective addition of lithiated ynamides to Ellman-Davis chiral imines is described. While additions of N-sulfonyl ynamides are highly stereoselective even without Lewis acids, the use of BF3-OEt2 completely reversed the stereoselectivity. In addition, oxazolidinone-substituted ynamides behaved differently and functioned better with BF3-OEt2, and the chirality of the oxazolidinone ring exerts no impact on the selectivity.
摘要
本文描述了手性亚胺与叶立德的高度非对映选择性加成反应。虽然 N-磺酰基叶立德的加成反应即使没有路易斯酸也具有高度的立体选择性，但使用 BF3-OEt2 完全改变了立体选择性。此外，恶唑烷酮取代的叶立德与 BF3-OEt2 反应表现出不同的行为，且效果更好，并且恶唑烷酮环的手性对选择性没有影响。
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