Asymmetric strecker synthesis of α-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary

被引：70

作者：

Boesten, WHJ ^{[1
]}

Seerden, JPG ^{[1
]}

de Lange, B ^{[1
]}

Dielemans, HJA ^{[1
]}

Eisenberg, HLM ^{[1
]}

Kaptein, B ^{[1
]}

Moody, HM ^{[1
]}

Kellogg, RM ^{[1
]}

Broxterman, QB ^{[1
]}

机构：

[1] Syncom BV, NL-9747 AT Groningen, Netherlands

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 08期

关键词：

D O I：

10.1021/ol007042c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective Strecker reactions based on (R)-phenylglycine amide as chiral auxiliary are reported, The Strecker reaction is accompanied by an in situ crystallization induced asymmetric transformation, whereby one diastereomer selectively precipitates and can be isolated in 76-93% yield and dr > 99/1. The diastereomerically pure a-amino nitrile obtained from pivaldehyde (R-1 = t.Bu, R-2 = H) was converted in three steps to (S)-tert leucine in 73% yield and >98% ee.

引用

页码：1121 / 1124

页数：4

共 33 条

[1]

BOESTEN WHJ, 1991, Patent No. 442585

[2]

BOESTEN WHJ, 1991, Patent No. 442584

[3] Synthesis and use of enantiomerically pure tert-leucine [J].