Enantioselective Nitroso Aldol Intramolecular Transesterification Cyclization Domino Reaction for Highly Effective Construction of Chiral Spirooxindoles. Issue 32 (12th October 2016)

• Record Type: Journal Article
• Authors: Ji, Shan‐Ping; Liu, Lin‐Wei; Chen, Feng; Ren, Hong‐Xia; Yang, Yu; Zhang, Zheng‐Bing; Peng, Lin; Wang, Li‐Xin
• Is Part Of: European journal of organic chemistry. Issue 32(2016)
• Page Start: 5437
• Page End: 5444
• Publication Date: 2016-10-12
• Subjects: Organocatalysis -- Synthetic methods -- Aldol reactions -- Cyclization -- Spiro compounds; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600884
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A catalytic asymmetric nitroso aldol intramolecular transesterification cyclization domino reaction between a C3 alkyl ester substituted oxindole and nitrosobenzene for the construction of chiral spirooxindoles was achieved in the presence of a chiral bifunctional tertiary amine thiourea catalyst and water. Optically active spirooxindoles were obtained in moderate yields (up to 76 %) and excellent enantioselectivities (up to 95 % ee ). Abstract : Catalytic asymmetric nitroso aldol intramolecular transesterification cyclization domino reaction of a C3 alkyl ester substituted oxindole and nitrosobenzene to construct optically active spirooxindoles was achieved by using a chiral bifunctional tertiary amine thiourea as catalyst and water as additive in moderate yields (up to 76 %) and high enantioselectivities (up to 96 % ee ).