Highly diastereoselective asymmetric syn-aldol reactions of (R)-(N-tosyl) phenylalaninol propionate-derived titanium enolate and bidentate aromatic and aliphatic aldehydes
Ghosh, Arun K. 1Gulliver, John P.1
扫码查看
点击上方二维码区域，可以放大扫码查看
作者信息
1. Purdue Univ
折叠
Abstract
Asymmetric aldol reactions of ester-derived titanium enolates of (R)-(N-tosyl)phenylalaninol propionate and bidentate aromatic aldehydes has been investigated. Substrate scope of this aldol reaction was examined with a variety of bidentate aromatic aldehydes to provide syn-aldol products with high diastereoselectivity and isolated yields. Both enantiomers of N-(tosyl)phenylalaninol are readily prepared from commercially available and optically active phenylalaninol. Mild saponification removed the chiral auxiliary and furnished optically active 8-hydroxy carboxylic acids.
Key words
Syn -aldol reactions/Titanium enolate/Diastereoselective synthesis/Bidentate
NSTL
Elsevier