Improved synthesis of proline-derived Ni(II) complexes of glycine:: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids

被引：86
|
作者：
Ueki, H [1 ]
Ellis, TK [1 ]
Martin, CH [1 ]
Boettiger, TU [1 ]
Bolene, SB [1 ]
Soloshonok, VA [1 ]
机构：
[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 18期
关键词：
D O I：
10.1021/jo0301494
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N-benzylprolyl)-amino] benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N'-benzylprolyl)amino]-4-methylbenzophenone (4-MeBPBP), (S)-2-[N-(N'-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)4-Me-BPBP] and [GlyNi(II)-5- NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).
引用
收藏
页码：7104 / 7107
页数：4
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