Diversity-oriented regioselective domino Michael/Aldol reaction of 3-ylideneoxindoles: A direct access to indanol-fused 3-oxindoles. Issue 11 (3rd June 2018)

• Record Type: Journal Article
• Authors: Wang, Dan-Dan; Wei, Qi-Di; Wang, Guan-Lian; Gong, Yi; Liu, Xiong-Li; Zhou, Gen; Zhou, Ying; Zhang, Jian-Fei
• Is Part Of: Synthetic communications. Volume 48:Issue 11(2018)
• Page Start: 1346
• Page End: 1353
• Publication Date: 2018-06-03
• Subjects: 3-Ylideneoxindoles -- diversity oriented synthesis -- domino Michael/Aldol reaction -- indanol-fused 3-oxindoles -- regioselective; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2018.1447672
• Languages: English
• ISSNs: 0039-7911

Abstract

ABSTRACT: A diversity-oriented molecular hybridization strategy has been utilized for the synthesis of 2, 3-disubstituted 1-indanol-fused 3-oxindoles through a regioselective domino Michael/Aldol reaction of 3-ylideneoxindoles1 with malononitrile or cyanacetate ethyle2 . Products bearing consecutive stereocenters consist of an oxindole moiety and an indanol core, were smoothly obtained in high yields (up to 92% yield) with good diastereoselectivity (up to 20:1). This protocol also represents the first construction of indanol-fused 3-oxindole scaffolds, thus leading to new knowledge in the fields of both molecular complexity and diversity-oriented synthesis (DOS) and the lead compound discovery. It is also worth mentioning that the reaction was completely regioselective and the competitive regioisomeric products4 or5 were not obtained in any case. GRAPHICAL ABSTRACT: