α-硅烷基取代的α-羟基乙酸的合成与应用。

Synthesis and use of alpha-silyl-substituted alpha-hydroxyacetic acids.

作者信息

Bolm Carsten, Kasyan Andrey, Heider Peter, Saladin Sandra, Drauz Karlheinz, Günther Kurt, Wagner Christoph

机构信息

Institute of Organic Chemistry, RWTH Aachen, Professor-Pirlet-Str. 1, D-52056 Aachen, Germany.

出版信息

Org Lett. 2002 Jun 27;4(13):2265-7. doi: 10.1021/ol025911n.

DOI:10.1021/ol025911n

PMID:12074683

Abstract

[reaction: see text] Rhodium-catalyzed oxygen transfer was used to generate benzyl 2-silyl-2-oxoacetates in good yields. The hydrogenation of these compounds led to chiral alpha-silyl-substituted alpha-hydroxyacetic acids. Resolution by means of HPLC using a chiral stationary phase afforded an enantiomerically pure representative of this class of compounds, which was successfully applied as a chiral ligand in an asymmetric aldol-type reaction.

摘要

[反应：见正文] 铑催化的氧转移反应被用于高产率地生成苄基2-硅基-2-氧代乙酸酯。这些化合物的氢化反应生成了手性α-硅基取代的α-羟基乙酸。使用手性固定相通过高效液相色谱法进行拆分，得到了这类化合物的对映体纯的代表物，该代表物成功地用作不对称羟醛型反应中的手性配体。