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

页码：1948 / 1951

页数：4

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