Asymmetric Synthesis of α-Allyl-α-Aryl α-Amino Acids by Tandem Alkylation/π-Allylation of α-Iminoesters

被引：53
|
作者：
Curto, John M. [1 ]
Dickstein, Joshua S. [1 ]
Berritt, Simon [1 ]
Kozlowski, Marisa C. [1 ]
机构：
[1] Univ Penn, Dept Chem, Penn Merck High Throughput Experimentat Lab, Philadelphia, PA 19104 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 07期
关键词：
N-ALKYLATION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIALKYLZINC REAGENTS; MANNICH REACTIONS; CRYSTAL-STRUCTURE; RECENT PROGRESS; PHASE-TRANSFER; ISOMERIZATION; KETONES;
D O I：
10.1021/ol500506t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first asymmetric synthesis of alpha-allyl-alpha-aryl alpha-amino acids by means of a three-component coupling of alpha-iminoesters, Grignard reagents, and cinnamyl acetate is reported. Notably, the enolate from the tandem process provides a much higher level of reactivity and selectivity than the same enolate generated via direct deprotonation, presumably due to differences in the solvation/aggregation state. A novel method for removal of a homoallylic amine protecting group delivers the free amine congeners. The alpha-allyl group offers a means to generate further valuable alpha-amino acid structures as exemplified by ring closing metathesis to generate a higher ring homologue of alpha-aryl-proline.
引用
收藏
页码：1948 / 1951
页数：4
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