Synthesis of C2 symmetric primary vicinal diamines. Double stereospecific mitsunobu reaction on the heterocyclic diols derived from tartaric acid

✍ Scribed by Jacek Skarżewski; Anil Gupta

• Book ID: 104361193
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 488 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00173-0

✦ Synopsis

Homochiral l-alkyl-3,4-dihydroxypyrrolidines, (S,S)-and (R,R)-5 were obtained by cyclization and reduction of both enantiomers of (+)-and (-)-tartaric acid, respectively. Also (S,S)-3,4-dihydroxytetrahydrofurane 6 was prepared from (+)-diethyl tartrate. All these heterocyclic vic-diols underwent twofold Mitsunobu reaction (Ph3P/DEAD/HN 3) followed by catalytic hydrogenation forming stereospecifically the corresponding primary vicinal diamines (R,R)-, (S,S)-2 and (R,R)-3. The absolute configuration of diamines 2, 3 was established by the exciton-coupling CD spectra of their N,N'-diphthaloyl derivatives. (~) 1997 Elsevier Science Ltd