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Stereoselective Nucleophilic Addition Reactions of Reactive Pseudopeptides
Author(s) -
Reetz Manfred T.,
Kanand Jürgen,
Griebenow Nils,
Harms Klaus
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199216261
Subject(s) - stereoselectivity , diastereomer , chemistry , chelation , nucleophile , nucleophilic addition , addition reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
D,L ‐Pseudopeptides of type 1 undergo 1,4‐additions with t Bu 2 CuLi/Me 3 SiCl 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 (CH 3 ) 2 CuLi.