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DOI: 10.1055/s-0030-1257948
Palladium-Catalyzed Asymmetric [3+2] Cycloadditions towards Pyrrolidines
B. M. Trost*, S. M. Silverman
Stanford University, USA
Publication History
Publication Date:
23 August 2010 (online)

Significance
The palladium-catalyzed [3+2]-trimethylenemethane (TMM) cycloaddition, a 30-year-old reaction, has seen a recent resurgence due to the development of asymmetric variants. One such transformation is the use of aldimines towards the synthesis of chiral pyrrolidines (J. Am. Chem. Soc. 2007, 129, 12398). A much greater challenge is the use of more bulky, electron-rich ketimine substrates, which would provide pyrrolidines containing a tetrasubstituted center. The authors report that using a cyano TMM donor and phosphoramidite ligands, a broad range of N-tosyl imines undergo [3+2] cycloadditions with excellent enantio- and diastereoselectivity.