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Construction of Enantiopure Pyrrolidine Ring System via Asymmetric [3 + 2]-Cycloaddition of Azomethine Ylides

✍ Scribed by Ganesh Pandey; Prabal Banerjee; Smita R. Gadre

Publisher
John Wiley and Sons
Year
2007
Weight
18 KB
Volume
38
Category
Article
ISSN
0931-7597

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## Abstract The first catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides with various sterically hindered Ξ±,Ξ±,β‐trisubstituted 2‐alkylidene‐cycloketones has been developed successfully with silver acetate/TF‐BiphamPhos complex for the construction of spiro heterocyclic compounds co

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1,3-Dipolar cycloaddition of D-glucose-derived azomethine ylides for the synthesis of chiral pyrrolidines accompanied an unexpected 1,2-elimination in the furanose moiety of the products. The C3 0 alkoxy/ hydroxy group of the furanose moiety was invariably eliminated under the reaction conditions. A