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

Authors
Boesten, WHJ Seerden, JPG de Lange, B Dielemans, HJA Eisenberg, HLM Kaptein, B Moody, HM Kellogg, RM Broxterman, QA
Citation
Whj. Boesten et al., Asymmetric strecker synthesis of alpha-amino acids via a crystallization-induced asymmetric transformation using (R)-phenylglycine amide as chiral auxiliary, ORG LETT, 3(8), 2001, pp. 1121-1124
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
8
Year of publication
2001
Pages
1121 - 1124
Database
ISI
SICI code
1523-7060(20010419)3:8<1121:ASSOAA>2.0.ZU;2-5
Abstract
Diastereoselective Strecker reactions based on (R)-phenylglycine amide as c hiral auxiliary are reported, The Strecker reaction is accompanied by an in situ crystallization induced asymmetric transformation, whereby one diaste reomer selectively precipitates and can be isolated in 76-93% yield and dr > 99/1. The diastereomerically pure a-amino nitrile obtained from pivaldehy de (R-1 = t.Bu, R-2 = H) was converted in three steps to (S)-tert leucine i n 73% yield and >98% ee.