Stereoselective Nucleophilic Addition Reactions of Reactive Pseudopeptides | Zendy

Reetz Manfred T. | Zendy; Kanand Jürgen | Zendy; Griebenow Nils | Zendy; Harms Klaus | Zendy

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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.

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