Practical, scalable, enantioselective synthesis of (2R,3R)-N-boc-2-amino-3-cyclohexyl-3-hydroxypropanoic acid

被引:7
作者
Alonso, N
Santacana, F
Rafecas, L
Riera, A
机构
[1] Parc Cientif Barcelona, Unitat Rec Sintesi Asimetr, Barcelona 08028, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
[3] Enantia, SL Parc Cient Barcelona, E-08028 Barcelona, Spain
关键词
D O I
10.1021/op0500761
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An enantioselective synthesis of (2R,3R)-2-(tert-butoxycarbonyl)amino-3-cyclohexyl-3-hydroxypropanoic acid has been described starting from enantiomerically enriched ethyl 3-cyclohexyl-2,3-dihydroxypropanoate, easily available by Sharpless asymmetric dihydroxylation. The key reaction is the direct preparation of a sulfate by diol treatment with sulfuryl chloride, thus avoiding ruthenium-catalyzed sulfite oxidation.
引用
收藏
页码:690 / 693
页数:4
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