Online citations, reference lists, and bibliographies.
Please confirm you are human
(Sign Up for free to never see this)
← Back to Search

Asymmetric Palladium-catalyzed Carboamination Reactions For The Synthesis Of Enantiomerically Enriched 2-(arylmethyl)- And 2-(alkenylmethyl)pyrrolidines.

D. N. Mai, J. Wolfe
Published 2010 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
The enantioselective synthesis of 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidine derivatives via Pd-catalyzed alkene carboamination reactions is described. These transformations generate enantiomerically enriched products with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines. The application of this method to a concise asymmetric synthesis of (-)-tylophorine is also discussed.
This paper references
10.1002/chem.200900477
Solvent-enhanced diastereo- and regioselectivity in the Pd(II)-catalyzed synthesis of six- and eight-membered heterocycles via cis-aminopalladation.
Árpád Balázs (2009)
10.1021/JO702167U
Chiral N-heterocyclic carbene--Pd(0)-catalyzed asymmetric diamination of conjugated dienes and triene.
L. Xu (2008)
10.1021/jo801631v
Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.
M. Bertrand (2008)
10.1021/jo801024h
Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.
W. Zeng (2008)
10.1002/ADSC.200390026
Monodentate phosphoramidites: A breakthrough in rhodium-catalysed asymmetric hydrogenation of olefins
M. Berg (2003)
10.2174/157340709787580928
Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.
S. Chemler (2009)
10.1021/JA060291X
Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.
Kai-Tai Yip (2006)
10.1039/b811068a
A general approach to triphenylenes and azatriphenylenes: total synthesis of dehydrotylophorine and tylophorine.
Andrew L. McIver (2008)
10.1021/jo1002032
Diastereoselective synthesis of hexahydro-3H-pyrrolyzin-3-ones through Pd-catalyzed carboamination.
L. Bagnoli (2010)
10.1021/ja9102259
Intramolecular alkene aminopalladation reactions of (dppf)Pd(Ar)[N(Ar(1))(CH(2))(3)CH=CH(2)] complexes. insertion of unactivated alkenes into Pd-N bonds.
Joshua D. Neukom (2010)
10.1021/JA0430346
Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.
Joshua E. Ney (2005)
10.1039/B607474J
Intramolecular aminopalladation of alkenes as a key step to pyrrolidines and related heterocycles.
A. Minatti (2007)
10.1021/JA0753389
Palladium-catalyzed asymmetric [3+2] cycloaddition of trimethylenemethane with imines.
B. Trost (2007)
10.1021/JA075041A
Oxidative diamination of alkenes with ureas as nitrogen sources: mechanistic pathways in the presence of a high oxidation state palladium catalyst.
K. Muñiz (2008)
10.1021/JA0762240
Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.
W. Zeng (2007)
10.1021/jo901778a
Enantioselective intramolecular oxidative aminocarbonylation of alkenylureas catalyzed by palladium-spiro bis(isoxazoline) complexes.
Tetsuya Tsujihara (2009)
10.1021/ol902348t
Pd(II)/(t)Bu-quinolineoxazoline: an air-stable and modular chiral catalyst system for enantioselective oxidative cascade cyclization.
Wei He (2009)
10.1021/OL0606435
A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.
M. Bertrand (2006)
10.1002/ANIE.200460060
Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.
Joshua E. Ney (2004)
10.1016/J.TET.2005.03.110
Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides
M. Bertrand (2005)
10.1021/JA074698T
Catalytic asymmetric diamination of conjugated dienes and triene.
H. Du (2007)
10.1021/JA070424U
Two-faced reactivity of alkenes: cis- versus trans-aminopalladation in aerobic Pd-catalyzed intramolecular aza-Wacker reactions.
G. Liu (2007)
10.1002/EJOC.200900920
Efficient and Chirally Specific Synthesis of Phenanthro‐Indolizidine Alkaloids by Parham‐Type Cycloacylation
Ziwen Wang (2010)
10.1055/S-2001-18703
Isolation, Total Synthesis and Biological Activity of Phenanthroindolizidine and Phenanthroquinolizidine Alkaloids
Z. Li (2004)
10.1021/CR020039H
The asymmetric intramolecular Heck reaction in natural product total synthesis.
A. Dounay (2003)
10.1002/EJOC.200600767
Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.
J. Wolfe (2007)
10.1021/ol902949d
Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole.
Venkata Jaganmohan Reddy (2010)
10.1021/jo902114u
A concise palladium-catalyzed carboamination route to (+/-)-tylophorine.
Lana M Rossiter (2009)
10.1016/J.TETLET.2003.11.108
Deprotection of a primary Boc group under basic conditions
N. J. Tom (2004)
10.1021/JA0680562
A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.
H. Du (2007)
10.1039/B300565H
Monodentate phosphoramidites; versatile ligands in catalytic asymmetric intramolecular Heck reactions
R. Imbos (2003)
10.1021/ol801168j
Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.
Y. Yasui (2008)
10.1002/anie.200903178
Synthesis of aziridines by palladium-catalyzed reactions of allylamines with aryl and alkenyl halides: evidence of a syn-carboamination pathway.
Sayuri Hayashi (2009)
10.1055/S-0028-1087339
Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.
J. Wolfe (2006)
10.1002/CHEM.200600592
Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.
A. Fürstner (2006)
10.1021/OM800064R
A Chiral Phosphoramidite beyond Monodentate Coordination: Secondary π-Interactions Turn a Dangling Aryl into a Two-, Four-, or Six-Electron Donor in d6 and d8 Complexes
I. Mikhel (2008)
10.1021/JM049243I
Discovery of 5-arylsulfonamido-3-(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists.
D. Cole (2005)
10.1016/J.TETASY.2004.05.038
Asymmetric palladium-catalyzed hydrosilylation of styrenes using efficient chiral spiro phosphoramidite ligands
X. Guo (2004)



This paper is referenced by
10.1021/ol4009848
Sultam synthesis via Cu-catalyzed intermolecular carboamination of alkenes with N-fluorobenzenesulfonimide.
Keiichi Kaneko (2013)
10.1039/C3RA47465H
Total synthesis of phenanthroindolizidine alkaloids via asymmetric deprotonation of N-Boc-pyrrolidine
Meng Deng (2014)
10.1002/EJOC.201100444
Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.
Monissa C. Paderes (2011)
10.1016/j.bmcl.2012.03.109
Synthesis of indolizidinone analogues of cytotoxic alkaloids: monocyclic precursors are also active.
A. Boto (2012)
10.1021/ol200784y
Enantioselective Pd(II)-catalyzed aerobic oxidative amidation of alkenes and insights into the role of electronic asymmetry in pyridine-oxazoline ligands.
R. I. McDonald (2011)
10.1039/c3cc40583d
A novel method to access chiral nonnatural 2,4-disubstituted pyrrolidines from aldehydes and nitroolefins only with an α-substituent.
B. Zheng (2013)
10.1002/ANGE.201907269
Intermolekulare, durch Cp*RhIII‐katalysierte C−H‐Aktivierung ermöglichte 1,4‐Carboaminierung von konjugierten Dienen
T. Pinkert (2019)
10.1002/anie.201911961
Asymmetric Wacker-Type oxyallenylation and Azaallenylation of Cyclic Alkenes.
J. Zhou (2019)
10.1039/C4QO00084F
Asymmetric synthesis of (S)-tylophorine and (S)-cryptopleurine via one-pot Curtius rearrangement and Friedel–Crafts reaction tandem sequence
F. Chen (2014)
10.1002/ADSC.201100220
Cobalt‐Catalyzed Carbon‐Carbon Bond Formation: Synthesis and Applications of Enantiopure Pyrrolidine Derivatives[1]
Shih Hsu (2011)
10.1007/7081_2012_98
Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions
J. Wolfe (2013)
10.1039/c4ob00200h
An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence.
Bo Su (2014)
10.1002/EJOC.201201472
The First Enantioselective Approach to 13a‐Methyl‐14‐hydroxyphenanthroindolizidine Alkaloids – Synthetic Studies towards Hypoestestatin 2
Bo Su (2013)
10.1021/jo402705w
Cu(OAc)₂-promoted cascade carboamination/oxidative cyclization of C-acylimines with alkenes.
Ling Dang (2014)
10.1021/acs.orglett.6b03410
Enantioselective Palladium-Catalyzed Oxidative Cascade Cyclization of Aliphatic Alkenyl Amides.
Wei Du (2017)
10.1002/anie.201912907
Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
Tuhin Patra (2019)
10.1039/C3SC51222C
Palladium-catalyzed heteroallylation of unactivated alkenes – synthesis of citalopram
J. Hewitt (2013)
10.1021/ol5004143
Cerium(IV) ammonium nitrate mediated three-component α-allylation of imine surrogates.
Mathieu Bekkaye (2014)
10.1039/d0cc03707a
Ligand-enabled gold-catalyzed 1,2-heteroarylation of alkenes.
Akash G Tathe (2020)
10.1021/jacs.5b10176
Catalytic Enantioselective Diarylation of Alkenes.
W. You (2015)
10.1002/anie.201402462
Enantioselective copper-catalyzed carboetherification of unactivated alkenes.
Michael T. Bovino (2014)
10.1021/jo302725q
An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence.
Bo Su (2013)
10.1002/anie.202012882
Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective 1,2-Arylfluorination of Internal Enamides.
Yang Xi (2020)
10.1002/chem.201801539
N-Heterocyclic Carbene-Catalyzed Annulation of α-Chloroaldehydes with γ-/δ-Amino-α,β-Unsaturated Ketones: Enantioselective Synthesis of Pyrrolidones and Piperidones.
Zhao-Fei Zhang (2018)
10.1002/anie.201205233
Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.
B. A. Hopkins (2012)
10.1002/cjoc.201900516
Palladium(II)‐Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N‐Protecting Groups
C. Chen (2020)
10.1002/cjoc.202000256
A journey to SPSiOL, a new type of chiral ligand scaffold
Hongchao Chen (2020)
10.1016/J.TET.2013.02.014
Concise synthesis of tylophorine
Qi-xian Lin (2013)
10.1021/ACS.JOC.6B01328
1,2-Disubstituted Alkenes as Migratory Insertion Participants in Zn(II)-Promoted Metalloamination/Cyclization of N,N-Dimethylhydrazinoalkenes.
Bryce Sunsdahl (2016)
10.1039/C8QO01076E
Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines
Baozhen Sun (2019)
10.1002/anie.201700889
Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N-H and Aryl C-H Bond Cleavage.
W. Zhang (2017)
10.1021/ol2029383
Pd(0)-catalyzed oxy- and aminoalkynylation of olefins for the synthesis of tetrahydrofurans and pyrrolidines.
Stefano Nicolai (2011)
See more
Semantic Scholar Logo Some data provided by SemanticScholar