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Stereoselective Nucleophilic Addition Reactions of Reactive Pseudopeptides

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Reetz,  Manfred T.
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Kanand,  Jürgen
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Griebenow,  Nils
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Reetz, M. T., Kanand, J., Griebenow, N., & Harms, K. (1992). Stereoselective Nucleophilic Addition Reactions of Reactive Pseudopeptides. Angewandte Chemie International Edition, 31(12), 1626-1629. doi:10.1002/anie.199216261.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0023-CA44-7
Abstract
D,L-Pseudopeptides of type 1 undergo 1,4-additions with tBu2CuLi/Me3SiCl with high stereoselectivity, whereas reactions of the corresponding L,L diastereomers are substantially less diastereoselective. The L,L,L and D,L,L analogues also react with different stereoselectivities. Strict chelation control plays a role in the Grignard-like reaction of L,L peptide aldehydes like 2 with (CH3)2CuLi.