Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation
Тип публикации: Journal Article
Дата публикации: 2008-09-06
SCImago Q1
Tоп 10% SCImago
WOS Q1
БС1
SJR: 5.491
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
18774811
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
The stereoselective synthesis of either trans- or cis-3,5-disubstituted pyrazolidines is accomplished via Pd-catalyzed carboamination reactions of unsaturated hydrazine derivatives. The products are obtained in good yield with up to >20:1 diastereoselectivity. Stereocontrol is achieved by modulating the degree of allylic strain in the transition state for syn-aminopalladation through a simple modification of the substrate N(2)-substituent. The pyrazolidine products can be further transformed to 3,5-disubstituted pyrazolines via deprotection/oxidation, or to substituted 1,3-diamines via N-N bond cleavage.
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Giampietro N. C., John A. Wolfe (2) J. S. Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation // Journal of the American Chemical Society. 2008. Vol. 130. No. 39. pp. 12907-12911.
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Giampietro N. C., John A. Wolfe (2) J. S. Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation // Journal of the American Chemical Society. 2008. Vol. 130. No. 39. pp. 12907-12911.
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TY - JOUR
DO - 10.1021/ja8050487
UR - https://doi.org/10.1021/ja8050487
TI - Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation
T2 - Journal of the American Chemical Society
AU - Giampietro, Natalie C
AU - John A. Wolfe (2), JOHN S.
PY - 2008
DA - 2008/09/06
PB - American Chemical Society (ACS)
SP - 12907-12911
IS - 39
VL - 130
PMID - 18774811
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2008_Giampietro,
author = {Natalie C Giampietro and JOHN S. John A. Wolfe (2)},
title = {Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation},
journal = {Journal of the American Chemical Society},
year = {2008},
volume = {130},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/ja8050487},
number = {39},
pages = {12907--12911},
doi = {10.1021/ja8050487}
}
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MLA
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Giampietro, Natalie C., and JOHN S. John A. Wolfe (2). “Stereoselective Synthesis of cis- or trans-3,5-Disubstituted Pyrazolidines via Pd-Catalyzed Carboamination Reactions: Use of Allylic Strain to Control Product Stereochemistry Through N-Substituent Manipulation.” Journal of the American Chemical Society, vol. 130, no. 39, Sep. 2008, pp. 12907-12911. https://doi.org/10.1021/ja8050487.
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