Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1‐Azabicyclo[5.3.0]decane Moiety. Issue 12 (7th September 2017)

• Record Type: Journal Article
• Authors: Meng, Xiangtai; Du, Yanlong; Zhang, Qi; Yu, Aimin; Zhang, Youquan; Jia, Jiru; Liu, Xiujie
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 12(2017)
• Page Start: 1719
• Page End: 1723
• Publication Date: 2017-09-07
• Subjects: 1-azabicyclo[5.3.0]decane derivatives -- azomethine ylides -- domino reactions -- nitrogen heterocycles -- spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700384
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Spirooxindoles bearing a 1‐azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5‐heterobicyclic systems in one step. Furthermore, cycloaddition of the in‐situ‐generated azomethine ylide only proceeded for alkenyl sulfone dipolarophiles. Abstract : Ylides with a twist : Spirooxindoles bearing a 1‐azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5‐heterobicyclic systems in one step. Furthermore, cycloaddition of the in‐situ‐generated azomethine ylide only proceeded for alkenyl sulfone dipolarophiles.