Chiral N-Phosphonyl Imine Chemistry: Asymmetric Synthesis of α-Alkyl β-Amino Ketones by Reacting Phosphonyl Imines with Ketone-Derived Enolates

被引：28
|
作者：
Ai, Teng [1 ]
Han, Jianlin [1 ]
Chen, Zhong-Xiu [1 ]
Li, Guigen [1 ]
机构：
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79401 USA
来源：
CHEMICAL BIOLOGY & DRUG DESIGN | 2009年 / 73卷 / 02期
关键词：
enolates; N-phosphonyl imines; phosphoramide; alpha-alkyl beta-amino ketones; SOLID-PHASE SYNTHESIS; MANNICH-TYPE REACTION; 1,3-AMINO ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; ALDEHYDES; SULFINIMINES;
D O I：
10.1111/j.1747-0285.2008.00771.x
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of new chiral syn-alpha-branched beta-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.
引用
收藏
页码：203 / 208
页数：6
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