Panchaud Philippe, Chabaud Laurent, Landais Yannick, Ollivier Cyril, Renaud Philippe, Zigmantas Sarunas
University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, 3000 Bern 9, Switzerland.
Chemistry. 2004 Aug 6;10(15):3606-14. doi: 10.1002/chem.200400027.
A novel reaction for the introduction of an azide moiety by means of a mild radical process is currently under development. Sulfonyl azides are suitable azidating agents for nucleophilic radicals, such as secondary and tertiary alkyl radicals. More electrophilic radicals, such as enolate radicals, do not react with sulfonyl azides. This feature allowed the development of efficient intra- and intermolecular carboazidations of olefins. Due to the versatility of the azido group, this reaction has an important synthetic potential, as already demonstrated by the preparation of the core of several alkaloids, particularly those containing an amino-substituted quaternary carbon center, such as FR901483.
一种通过温和自由基过程引入叠氮基团的新型反应目前正在开发中。磺酰叠氮化物是亲核自由基（如仲烷基和叔烷基自由基）适用的叠氮化试剂。亲电性更强的自由基（如烯醇盐自由基）不与磺酰叠氮化物反应。这一特性使得烯烃的分子内和分子间高效碳叠氮化反应得以开发。由于叠氮基团的多功能性，该反应具有重要的合成潜力，已经通过几种生物碱核心结构的制备得到了证明，特别是那些含有氨基取代季碳中心的生物碱，如FR901483。
