N-heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole. Issue 6 (15th December 2014)

• Record Type: Journal Article
• Authors: Xie, Yuanwei; Que, Yonglei; Li, Tuanjie; Zhu, Ling; Yu, Chenxia; Yao, Changsheng
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 6(2015)
• Page Start: 1829
• Page End: 1835
• Publication Date: 2014-12-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob01706d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon with high diastereoselectivies. Abstract : A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon in moderate to good yields with high diastereoselectivities. The easy availability of the starting materials, the concise assembly and the potential utilization value of the products make this strategy attractive in molecular biology and pharmacy.