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Investigation of Synthetic Routes towards Derivatives of 3‐(Phenylsulfonimidoyl)propanoic Acid
Author(s) -
Tye Heather,
Skinner Catharine L.
Publication year - 2002
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 - 10.1002/1522-2675(200210)85:10<3272::aid-hlca3272>3.0.co;2-p
Subject(s) - chemistry , propanoic acid , hydroxylamine , intramolecular force , derivative (finance) , sulfoxide , reagent , stereochemistry , combinatorial chemistry , organic chemistry , financial economics , economics
The synthesis of a range of 3‐(phenylsulfonimidoyl)propanoate derivatives is described. A number of strategies for the imination of the key sulfoxide methyl 3‐(penylsulfinyl)propanoate are discussed including the use of O ‐(mesitylsulfonyl)hydroxylamine (MSH) and iminoiodane reagents (PhINSO 2 R). A successful strategy for the preparation of the target compounds was the use of MSH followed by in situ coupling with a N ‐Boc‐protected amino acid. The pseudo‐dipeptides thus formed exhibited interesting conformational properties in CDCl 3 solution giving evidence of intramolecular H‐bonds in all cases, except for the proline derivative.