Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine
Publication type: Journal Article
Publication date: 1988-06-01
Inorganic Chemistry
Abstract
Ausgehend von (3R,4R)-3,4-Bis(diphenylphosphino)pyrrolidin (1a), bzw. dem N-Benzyl-Derivat 1b wurden [P(R,S),3R,4R,P′-(R,S)]-3,4-Bis(phenylphosphino)pyrrolidin (2a-*) und dessen N-Benzyl-Derivat 2b-* als Diastereomerengemische hergestellt. Aus 2a-* wurde isomerenreines (PR,3R,4R,P′S)-3,4-Bis(benzylphenyl-phosphino)pyrrolidin (3a-3) dargestellt. [P(R,S), 3R,4R, P′(R,S)]-3,4-Bis(methylphenylphosphino)pyrrolidin (4a-*) wurde aus 2a-* als Diastereomerengemisch erhalten, dessen Auftrennung uber die Palladiumkomplexe der N-tert-Butoxycarbonyl-Derivate 8c-* gelang. [(PS, 3R4R,P′S)-1-(tert-Butoxycarbonyl)-3,4-bis(methylphenylphosphino) pyrrolidin-P,P′]diiodopalladium(II) (8c-1) und zum Vergleich [(3R,4R)-1-Benzyl-3,4-bis(diphenylphosphino)pyrrolidin-P,P′] (1,5-cyclooctadien)rhodium(I)-tetrafluoroborat (11) wurden durch Rontgenstrukturanalyse charakterisiert.
Enatioselective catalysis, 5. — New Ligands with four Stereogenic Centers. Synthesis and Separation of the Separation of the three Diastereomeric [P(R,S),3R,4R,P′(R,S]-3,4-Bis(methylphenylphosphino)-pyrrolidines
From (3R,4R)-3,4-bis(diphenylphosphino)pyrrolidine (1a) or the N-benzyl derivative 1b [P(R,S),3R,4R,P′-(R,S)]-3,4-bis(phenylphosphino)pyrrolidin (2a-*) resp. its N-benzyl derivative 2b-* were prepared as diastereomeric mixture. From 2a-* isomerically pure (PR,3R,4R,P′S)-3,4-bis(benzylphenyl-phosphino)pyrrolidin (3a-3) was prepared. [P(R,S), 3R,4R, P′(R,S)]-3,4-bis(methylphenylphosphino)pyrrolidin (4a-*), obtained from 2a-*, was a mixture of the three possible diastereomers. This mixture could be separated through the palladium complexes of the N-tert-butoxycarbonyl derivatives 8c-*. [(PS, 3R4R,P′S)-1-(tert-Butoxycarbonyl)-3,4-bis(methylphenylphosphino) pyrrolidin-P,P′]diiodopalladium(II) (8c-1) and for comparison [(3R,4R)-1-benzyl-3,4-bis(diphenylphosphino) pyrrolidine-P,P′](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (11) were characterised by X-ray crystallography.
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Nagel U., Rieger B. Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine // Chemische Berichte. 1988. Vol. 121. No. 6. pp. 1123-1131.
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Nagel U., Rieger B. Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine // Chemische Berichte. 1988. Vol. 121. No. 6. pp. 1123-1131.
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TY - JOUR
DO - 10.1002/cber.19881210617
UR - https://doi.org/10.1002/cber.19881210617
TI - Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine
T2 - Chemische Berichte
AU - Nagel, Ulrich
AU - Rieger, B.
PY - 1988
DA - 1988/06/01
PB - Wiley
SP - 1123-1131
IS - 6
VL - 121
SN - 0009-2940
ER -
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@article{1988_Nagel,
author = {Ulrich Nagel and B. Rieger},
title = {Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine},
journal = {Chemische Berichte},
year = {1988},
volume = {121},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/cber.19881210617},
number = {6},
pages = {1123--1131},
doi = {10.1002/cber.19881210617}
}
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Nagel, Ulrich, and B. Rieger. “Enantioselektive Katalyse, 5. Neue Liganden mit vier Stereozentren. Synthese und Trennung der drei diastereomeren [P( R,S ),3 R ,4 R ,P′( R,S )]‐3,4‐Bis(methylphenylphosphino)‐pyrrolidine.” Chemische Berichte, vol. 121, no. 6, Jun. 1988, pp. 1123-1131. https://doi.org/10.1002/cber.19881210617.