通过有机金属的极性翻转加成实现α-亚胺酯的三组分偶联：α,α-二取代α-氨基酸的合成
Three component coupling of alpha-iminoesters via umpolung addition of organometals: synthesis of alpha,alpha-disubstituted alpha-amino acids.
作者信息
Dickstein Joshua S, Fennie Michael W, Norman Amber L, Paulose Betty J, Kozlowski Marisa C
机构信息
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Am Chem Soc. 2008 Nov 26;130(47):15794-5. doi: 10.1021/ja8073006.
The synthesis of alpha,alpha-disubstituted alpha-amino acids by means of a three component coupling is reported. The coupling occurs through umpolung addition of organometallic reagents to the nitrogen of alpha-iminoesters. The resulting enolate intermediates subsequently react with electrophiles (aldehydes, imines, alpha,beta-unsaturated nitro, alkyl halides, acyl cyanides) to form a quaternary center. Tethering of the electrophile and nucleophile components provides cyclic alpha,alpha-disubstituted alpha-amino acid derivatives.
报道了通过三组分偶联合成α,α-二取代α-氨基酸的方法。该偶联反应通过将有机金属试剂对α-亚胺酯的氮进行极性翻转加成来实现。生成的烯醇盐中间体随后与亲电试剂（醛、亚胺、α,β-不饱和硝基化合物、卤代烃、酰基氰化物）反应形成季碳中心。亲电试剂和亲核试剂组分的连接提供了环状α,α-二取代α-氨基酸衍生物。
Zotero 插件