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.
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收藏
页码：1907 / 1910
页数：4
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