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Enantioselective Catalysis, XIII . Preparative and Structural Chemistry of Chiral 3‐(Diphenylphosphanyl)‐pyrrolidiens and Their Palladium(II) Complexes
Author(s) -
Nagel Ulrich,
Nedden Hans Günter
Publication year - 1997
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19971300313
Subject(s) - chemistry , norbornane , bicyclic molecule , enantioselective synthesis , enantiomer , epimer , stereochemistry , ligand (biochemistry) , palladium , catalysis , medicinal chemistry , organic chemistry , biochemistry , receptor
The preparation of both enantiomers of 3‐diphenylphosphanulpyrrolidiine ( 2 ) and several N ‐substituted derivatives together with two Pd Ii complexes of this ligand is reported. Form L‐malic acid and L‐hydroxyproline both enantiomers of 3‐hydroxypyrrolidine are prepared without any problems due to epimerization. KPPh 2 in the presence of LiCl is shown to be the most effective reagent for the synthesis of 2 . The reported X‐ray structure determination sof Pdl 2 complexes show a rather rigid bicyclic hetero‐norbornane skeleton. The flexibility of the other parts of the molecules is obvious in several polymorphs revealed by this method. This polymorphism is additionally investigated by a 31 P‐CP‐MAS study. From solution 1 ‐, 13 C‐ and 31 P‐NMR studies it is concluded that the bicyclic hetero‐norbornane skeleton is retained in solution.