Asymmetric synthesis of (S)-α-methyl α-amino acids by alkylation of chiral 3,6-dihydro-2H-1,4-oxazin-2-ones using unactivated alkyl halides and organic bases

被引：30

作者：

Chinchilla, R ^{[1
]}

Galindo, N ^{[1
]}

Nájera, C ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(98)00288-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

3,6-Dihydro-2H-1,4-oxazin-2-ones 1 have been diastereoselectively (>96% de) alkylated using unactivated alkyl halides and organic bases such as 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature in the presence of LiI. Hydrolysis of the resulting alkylated systems afforded enantiomerically enriched (S)-alpha-methyl alpha-amino acids. When 1,3-diiodopropane was used, spontaneous N-alkylation also took place giving bicyclic oxazinone 6 which was hydrolyzed to (S)-alpha-methylproline. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2769 / 2772

页数：4

共 39 条

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (07) : 1244 - 1263
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