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The Chiral Glycine Enolate Derivative from 1‐Benzoyl‐2‐( tert ‐butyl)‐3‐methyl‐1,3‐imidazolidin‐4‐one is Alkylated in the 5‐Position with Relative Topicity lk . Preliminary Communication
Author(s) -
Seebach Dieter,
Miller David D.,
Müller Stefan,
Weber Theodor
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680418
Subject(s) - chemistry , alkylation , glycine , benzyl bromide , acetone , enantioselective synthesis , alanine , serine , stereochemistry , bromide , derivative (finance) , medicinal chemistry , organic chemistry , amino acid , catalysis , biochemistry , financial economics , economics , enzyme
An overall enantioselective substitution of the R‐group of an α‐hydroxy‐ or α‐amino acid 1 [RCH(XH)COOH] by another R‐group is possible through heterocycles 2 obtained from 1 with pivaladehyde ( 1 → 7 ). The rac ‐ and the ( S )‐(+)‐heterocycles 8 (title compounds of type 5 ) are prepared from glycine and O ‐benzyl‐( S )‐serine, respectively. Their enolates ( cf. 9 , type 6 ) are alkylated with iodomethane, iodobutane, 2‐iodopropane, benzyl bromide, and acetone to give the trans ‐disubstituted imidazolidinones 10 with ≥ 95% diastereoselectivity. The configuration of the products is established by chemical correlation with alanine, phenylalanine, and valine.