General Protocols for the Synthesis of C(2)-Symmetric and Asymmetric 2,8-Disubstituted Analogues of Tröger's Base via Efficient Bromine-Lithium Exchanges of 2,8-Dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine.

Summary, in English

Methods for facile synthesis of symmetric and unsymmetric functionalized analogues of Tröger's base were developed with use of 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (2) as the starting material. C(2)-symmetric 2,8-disubstituted analogues of Tröger's base (4a-f) were synthesized via double bromine-lithium exchange of 2 followed by quench with electrophiles. Desymmetrization via single bromine-lithium exchange of 2, followed by quench with electrophiles, afforded asymmetric analogues of Tröger's base (6a-g). Further reaction of 2-bromo-8-(trimethylsilyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (6b) produced 7a-c via single bromine-lithium exchange and subsequent quench with electrophiles.

• Författare: Jacob Jensen; Johan Tejler; Kenneth Wärnmark
• Avdelning/ar: Centrum för analys och syntes
• Publiceringsår: 2002
• Språk: Engelska
• Sidor: 6008-6014
• Publikation/Tidskrift/Serie: Journal of Organic Chemistry
• Volym: 67
• Issue: 17
• Länkar: http://dx.doi.org/10.1021/jo025823g
• Dokumenttyp: Artikel i tidskrift
• Förlag: The American Chemical Society (ACS)
• Ämne: Organic Chemistry
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 1520-6904