Stereoselective Nucleophilic Addition Reactions of Reactive Pseudopeptides

Reetz, Manfred T.; Kanand, Jürgen; Griebenow, Nils; Harms, Klaus

doi:10.1002/anie.199216261

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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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引用

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

引用: https://hdl.handle.net/11858/00-001M-0000-0023-CA44-7

要旨

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.