A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand

被引：14
|
作者：
Shimizu, Hideki [1 ,2 ]
Holder, Jeffrey C. [1 ]
Stoltz, Brian M. [1 ]
机构：
[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA
[2] Shionogi & Co Ltd, Amagasaki, Hyogo 6600813, Japan
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
关键词：
asymmetric catalysis; diamine ligands; optimization; synthesis; ASYMMETRIC CATALYSIS; (Z)-4'-ACETOXY-2'-BUTENYL 2-ALKYNOATES; CYCLIZATION; HYDROSILYLATION; KETONES;
D O I：
10.3762/bjoc.9.187
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand has been developed. Inconsistent yields and tedious purification in known routes to (S)-t-BuPyOx suggested the need for an efficient, dependable, and scalable synthetic route. Furthermore, a route suitable for the synthesis of PyOx derivatives is desirable. Herein, we describe the development of a three-step route from inexpensive and commercially available picolinic acid. This short procedure is amenable to multi-gram scale synthesis and provides the target ligand in 64% overall yield.
引用
收藏
页码：1637 / 1642
页数：6
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