Stabilizing effect of intramolecular lewis base toward racemization of optically active selenoxides
✍ Scribed by Takahiro Soma; Toshio Shimizu; Kazunori Hirabayashi; Nobumasa Kamigata
- Publisher
- John Wiley and Sons
- Year
- 2007
- Tongue
- English
- Weight
- 430 KB
- Volume
- 18
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20299
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✦ Synopsis
Abstract
2‐(Methylchalcogenomethyl)diphenyl selenoxides 1 and 2‐{2′‐(N,N‐dimethylamino)ethyl}phenyl alkyl (or aryl) selenoxides 2, which were expected to be stabilized toward racemization by intramolecular coordination, were synthesized and optically resolved into their enantiomers on an optically active column using high‐performance liquid chromatography. Relationship between the absolute configurations and the chiroptical properties of the enantiomers was clarified by comparing with those of sulfur analogues. Stabilities toward racemization of optically active selenoxides 1a and 1b were nearly equal to that of 2‐{(N,N‐dimethylamino)methyl}diphenyl selenoxide and mesityl phenyl selenoxide. The rates of racemization for optically active selenoxides 2 were found to be faster than that of 2‐{(N,N‐dimethylamino)methyl}phenyl alkyl (or aryl) selenoxides. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:301–311, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20299