Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids

被引:115
作者
Cutting, Gary A.
Stainforth, Nikki E.
John, Matthew P.
Kociok-Koehn, Gabriele
Willis, Michael C. [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
[2] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[3] GlaxoSmithKline, Chem Dev Div, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/ja073473f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anti-configured protected alpha,beta diamino acids are prepared with up to 99% ee using a direct catalytic enantioselective Mannich reaction. A catalyst system incorporating a chiral bis (oxazoline) ligand, Mg(ClO4)(2) and HOnigs base, promotes the addition of an isothiocyanate-substituted imide to a variety of aryl-, heteroaryl-, alkenyl-, and alkyl-derived imines. Conversion of the products to their i Pr-ester derivatives allows epimerization to the syn -diastereomers.
引用
收藏
页码:10632 / +
页数:3
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