Pseudopeptidic sulfoxides: relative stability and absolute configuration of diastereomers

✍ Scribed by Jean-Marc Poudrel; Peter Karuso

• Book ID: 104210631
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 111 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01003-0

✦ Synopsis

The relative stability in solution of diastereomeric pseudopeptidic sulfoxides initially designed as FKBP inhibitors is used to assign the absolute con®guration at the sulfur atom. Decomposition is shown to occur via b-elimination of the corresponding sulfenic acid and alkene. Complementary studies including molecular mechanics, 1 H NMR spectroscopy and optical rotation con®rm that the (R)-isomer is the most stable, presumably due to non-bonded interactions favouring a low energy conformation where decomposition is precluded.