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Investigation of Synthetic Routes towards Derivatives of 3-(Phenylsulfonimidoyl)propanoic Acid

✍ Scribed by Heather Tye; Catharine L. Skinner

Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
136 KB
Volume
85
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday

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 (PhÀINÀSO 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.

1 ) Also known as sulfoximide or sulfoximine.

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