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Organic Letters
Letter
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Scheme 2. Synthesis of Pyrrole from Pyrrolidine
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In conclusion, we have developed an efficient, operationally
simple protocol for the synthesis of 5,5-fused bicyclo-
pyrrolidine by desymmetrization of prochiral cyclopentene-
dione via [3 + 2] cycloaddition of azomethine ylide catalyzed
by a silver(I)−ferrophox complex. A variety of bicyclic-
pyrrolidine derivatives were synthesized in good yields (up to
76%) and excellent enantioselectivities (up to 98%) under mild
reaction conditions. The synthetic potential of this desymmet-
rization approach has also been shown by the synthesis of
bicyclic-pyrrole in a highly enantio-/diastereoselective manner.
Mechanistic investigation and further applications of this
chemistry are actively ongoing.
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, R. G.; Carretero, J. C. J. Am. Chem. Soc.
, R. G.; Carretero, J. C. Org.
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ASSOCIATED CONTENT
* Supporting Information
■
(e) Lop
130, 10084. (f) Lop
́
ez-Per
́
ez, A.; Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2008,
ez-Perez, A.; Adrio, J.; Carretero, J. C. Angew.
S
́
́
The Supporting Information is available free of charge on the
Chem., Int. Ed. 2009, 48, 340. (g) Filippone, S.; Maroto, E. E.; Martín-
Domenech, A.; Suarez, M.; Martín, N. Nat. Chem. 2009, 1, 578.
(h) Kim, H. Y.; Shih, H.-Y.; Knabe, W. E.; Oh, K. Angew. Chem., Int.
Ed. 2009, 48, 7420. (i) Antonchick, A. P.; Gerding-Reimers, C.;
Catarinella, M.; Schurmann, M.; Preut, H.; Ziegler, S.; Rauh, D.;
Waldmann, H. Nat. Chem. 2010, 2, 735. (j) Teng, H.-L.; Huang, H.;
Tao, H.-Y.; Wang, C.-J. Chem. Commun. 2011, 47, 5494.
Experimental procedures, characterization data for all
new compounds, and copies of 1H and 13C NMR spectra
and HPLC chromatogram for all new compounds (PDF)
X-ray crystal structure data for compound 4p (CIF)
(8) (a) Melhado, A. D.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc.
́
2007, 129, 12638. (b) Martín-Rodríguez, M.; Najera, C.; Sansano, J.
AUTHOR INFORMATION
Corresponding Author
M.; Wu, F.-L. Tetrahedron: Asymmetry 2010, 21, 1184.
(9) (a) Shi, J.-W.; Zhao, M.-X.; Lei, Z.-Y.; Shi, M. J. Org. Chem. 2008,
73, 305. (b) Arai, T.; Yokoyama, N.; Mishiro, A.; Sato, H. Angew.
Chem., Int. Ed. 2010, 49, 7895. (c) Awata, A.; Arai, T. Chem. - Eur. J.
2012, 18, 8278.
■
Notes
(10) (a) Chen, X.- H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J.
Am. Chem. Soc. 2009, 131, 13819. (b) Yu, J.; Chen, W.-J.; Gong, L.-Z.
Org. Lett. 2010, 12, 4050. (c) Wang, C.; Chen, X.-H.; Zhou, S.-M.;
Gong, L.-Z. Chem. Commun. 2010, 46, 1275. (d) Shi, F.; Luo, S.-W.;
Tao, Z.-L.; He, L.; Yu, J.; Tu, S.-J.; Gong, L.-Z. Org. Lett. 2011, 13,
4680. (e) Lin, S.; Deiana, L.; Zhao, G.-L.; Sun, J.; Cordova, A. Angew.
Chem., Int. Ed. 2011, 50, 7624.
(11) Liu, K.; Teng, H.-L.; Yao, L.; Tao, H.-Y.; Wang, C.-J. Org. Lett.
2013, 15, 2250.
(12) CCDC 1414281 for 4p; see Supporting Information for details
(13) Dai, L.; Xu, D.; Tang, L.-W.; Zhou, Z.-M. ChemCatChem 2015,
7, 1078.
(14) Stereochemistry of minor isomer has been studied from NOE
experiments. For details, see the Supporting Information.
(15) (a) Arrieta, A.; Otaegui, D.; Zubia, A.; Cossío, F. P.; Diaz-Ortiz,
A.; de la Hoz, A.; Herrero, M. A.; Prieto, P.; Foces-Foces, C.; Pizarro,
J. L.; Arriortua, M. I. J. Org. Chem. 2007, 72, 4313. (b) Robles-Machín,
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
V.K.S. thanks the DST for a research grant through a J. C. Bose
Fellowship. T.D. and P.S. thank IISER Bhopal for their
fellowship. We thank Dr. Vishnumaya Bisai, IISER Bhopal, for
proof-reading this manuscript. We thank Dr. Alakesh Bisai,
IISER Bhopal, for fruitful suggestions. We thank Mr. Lalit
Mohan Jha, IISER Bhopal, for single crystal XRD analysis.
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DOI: 10.1021/acs.orglett.5b02582
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