Abstract
β-hydroxy-α-amino esters are found in various bioactive natural. 1 On the other hand non proteinogenic amino acids play a vital role in the syntheses of various bioactive compounds and drugs. For example “DOPA” is employed against Parkinson’s disease. 2 Thus, both of their biological and synthetic role make them attractive for synthetic and medicinal community. Thus the goal of our work is a diastereoselective syntheses of the β-hydroxyα-amino esters, non-proteinogenic amino acids including racemic “DOPA” from MBH adducts.
Highlights
Our work begins with preparation of MBH adducts 111.3 the adducts [1-7], were silylated to give products [12-18] and the adducts [3, 4, 6] and [8-11] were acetylated[2] to give products [19-25]
*The diastereoselectivity was determined by analysis of H1 NMR of the crude reaction mixture
The above methodology allowed us to develop an efficient preparation of the DOPA
Summary
Our work begins with preparation of MBH adducts 111.3 the adducts [1-7], were silylated to give products [12-18] and the adducts [3, 4, 6] and [8-11] were acetylated[2] to give products [19-25]. The later (19-25) were deacetylated to provide metacrylate derivatives [26-32] (Table 1). 6, 3-Cl-Ph 20, 92 27, 95 diastereoselectivity (anti:syn >95:5) and aminoesters
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