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Selective Reactions, Resolution and Absolute Configuration of Bridged Hydroazulenes

✍ Scribed by Werner Tochtermann; Torsten Panitzsch; Melanie Petroll; Thorsten Habeck; Axel Schlenger; Christian Wolff; Eva-Maria Peters; Karl Peters; Hans Georg von Schnering

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
257 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

Treatment of the bridged oxepine (±)-1 with a large excess epoxides (±)-5 and (±)-6. The resolution of the hydroazulenone (±)-2 is achieved by fractional crystallization of of powdered sodium methoxide in Et 2 O or with triphenylphosphonium methylide leads to the functionalized the quinine salt (؊)-8 of the corresponding mono acid (±)-7.

The absolute configuration of (+)-7 is established by X-ray hydroazulenes (±)-2 (69%) and (±)-3 (81%). Regioselective and stereoselective cyclopropanation of (±)-2 leads to the analysis of the quinine salt (؊)-8. dibromocyclopropane derivative (±)-4. Epoxidation gives the

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Optical resolution and absolute configur
Optical resolution and absolute configuration of N-Benzyloxycarbonyl-Ξ±-alkoxyglycines
✍ Masao Kawai; Keiichi Yamada; Kouji Hosoda; Yasuhiro Omori; Shuji Kato; Nobuhiro πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 129 KB πŸ‘ 1 views

Optical resolution of racemic N-benzyloxycarbonyl-protected alpha-alkoxyglycines, (+/-)-Cbz-Gly(OR)-OH (R = Et and Pr(i)), was achieved by means of fractional crystallization of diastereomeric salts with (+)-(1S,2S)-2-amino-1-phenyl-1,3-propanediol or diastereomeric esters of (+)- or (-)-menthol. Th