✦ LIBER ✦
Retention stereochemistry in ligand coupling reaction of optically active (1 R)-phenylethyl 2-quinolyl (R)- and (S)-sulfoxide with methylmagnesium bromide
✍ Scribed by Jun'ichi Uenishi; Atsumi Yamamoto; Takashi Takeda; Shoji Wakabayashi; Shigeru Oae
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 520 KB
- Volume
- 3
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
Reactions of-( + )--(I R)-phenybthyl 2-quinolyl (R)-
sulfbxide 7a and ( --)-(I R)-phenylethyl2-quinolyl (S)sulfbxide 7b with methylmagnesium bromide were examined. The reaction gave (R)-Z-(Z-phenyle-thy1)quinoline 9 as a ligand-coupling product, and a mixture of methyl(1R)-phenylethyl (R)and (S)-sulfoxide 1 l a and 1 l b as ligand exchange products. The other (S) stereoisomer at the I -phenylethyl carbon center was not detected i n the reaction products. That is, both the ligand coupling and ligand exchange reactions proceeded with retention of configuration at the asymmetric carbon center.