Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids

被引：37
|
作者：
Roers, R [1 ]
Verdine, GL [1 ]
机构：
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 21期
关键词：
catalytic aldol; Curtius rearrangement; beta-amino acid;
D O I：
10.1016/S0040-4039(01)00457-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported here is an efficient procedure for enantio- and diastereoselective synthesis of purr beta -amino acids that display a tert-hydroxyl functionality in the alpha -position. Key steps include a catalytic asymmetric aldol reaction and a modified Curtius rearrangement to form oxazolidinone intermediates, which are chemoselectively opened to furnish N-protected alpha -hydroxy-alpha -methyl-beta -amino acids. A modified work-up procedure of the: aldol reaction allows for recovery of up to 90% of bisoxazolinyl ligands from the catalysts. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3563 / 3565
页数：3
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