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ASYMMETRIC NUCLEOPHILIC ACYLATION WITH METALATED AMINO NITRILES - DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-AROYLCYCLOHEXANONES VIA TANDEM MICHAEL ADDITION/ALPHA-ALKYLATION
被引：0
作者：
ENDERS, D
KIRCHHOFF, J
MANNES, D
RAABE, G
机构：
来源：
SYNTHESIS-STUTTGART
|
1995年
/
06期
关键词：
ASYMMETRIC SYNTHESIS;
AMINO NITRILES;
NUCLEOPHILIC ACYLATION;
MICHAEL ADDITION;
1,4-DIKETONES;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ;
081704 ;
摘要：
Tandem conjugate addition/alpha-alkylation of lithiated chiral alpha-amino nitriles 3 and alkyl bromides to 2-cyclohexenone afforded 2-substituted 3-aroylcyclohexanones 5 of high diastereo- and enantiomeric purity (de greater than or equal to 98 %, ee greater than or equal to 97 - greater than or equal to 99 %) and in good overall yields. The absolute configuration of the new stereogenic centres was determined by X-ray structure analysis of the Michael adduct 4c.
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页码：659 / 666
页数：8
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