Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides: A Possible Intermediate Characterized

被引：28
|
作者：
Lecachey, Baptiste [1 ,2 ]
Duguet, Nicolas [1 ,2 ]
Oulyadi, Hassan [1 ,2 ]
Fressigne, Catherine [1 ,2 ]
Harrison-Marchand, Anne [1 ,2 ]
Yamamoto, Yasutomo [3 ]
Tomioka, Kiyoshi [3 ]
Maddaluno, Jacques [1 ,2 ]
机构：
[1] Univ Rouen, IRCOF, CNRS, UMR 6014, F-76821 Mont St Aignan, France
[2] Univ Rouen, FR 3038, F-76821 Mont St Aignan, France
[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 09期
关键词：
DIISOPROPYLAMIDE-MEDIATED ENOLIZATIONS; MIXED AGGREGATION; N-BUTYLLITHIUM; NMR; COMPLEXES; SPECTROSCOPY; HALIDES;
D O I：
10.1021/ol900275y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two 1:1 noncovalent mixed aggregates between a lithium enolate and two diastereomeric lithium amides have been identified spectroscopically in THE The NMR data, as well as DFT theoretical calculations, shine some light on a puzzling reversal of induction, observed when switching from one diastereomer of the amide to the other in the enantioselective Michael addition of the lithium enolate to an unsaturated ester.
引用
收藏
页码：1907 / 1910
页数：4
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