TY - ECHAP DO - 10.1055/sos-SD-211-00033 SN - 9783131728319 SN - 9783132064317 LA - EN AU - Raghunathan,R.; Purushothaman,S. TI - 2.1.6 [3 + 2] Cycloaddition as the Key Step PB - Georg Thieme Verlag KG CY - Stuttgart PY - 2014 ET - 1st edition UR - http://www.thieme-connect.de/products/ebooks/lookinside/10.1055/sos-SD-211-00033 T3 - Science of Synthesis VL - 2013/6 DA - 2015/10/23 KW - azomethine ylides KW - [3 + 2]-cycloaddition reactions KW - 1,3-dipoles KW - spiro-fused pyrrolidines KW - stereoselective synthesis KW - α, β-unsaturated carbonyl compounds AB - α, β-Unsaturated carbonyl compounds, which act as dipolarophiles in [3 + 2]-cycloaddition reactions with azomethine ylides, have been used for the highly regio- and stereoselective construction of heterocycles such as spiro-fused pyrrolidines. Azomethine ylides generated from isatin (1H-indole-2,3-dione) and cyclic and acyclic α-amino acids are considered to be important 1,3-dipoles, since their cycloaddition to α, β-unsaturated carbonyl compounds leads to the formation of spiro[indoline-3,2′-pyrrolidin]-2-ones, which form the basic building units of several natural and biologically active compounds. T2 - Multicomponent Reactions, Volume 2 ER -