Organic Letters
Letter
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The development of asymmetric variants of the reaction with
such a strategy is underway and will be reported in due course.
In summary, we have realized an atom-economic Pd(II)-
catalyzed addition/alkyne−allene isomerization/IMDA reac-
tion, providing a highly efficient synthesis of complex oxygen
bicycles with diversified functional groups and structural motifs.
The reaction is regio- and stereoselective, proceeds in a highly
ordered fashion, and employs readily available substrates. Due
to the unique reactivity of allene intermediates, we believe that
this conceptually intriguing addition−isomerization sequence
will open up new opportunities to access valuable compounds.
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ASSOCIATED CONTENT
* Supporting Information
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S
Experimental procedures, DFT calculation data, character-
ization of the products, CIF file. This material is available free
AUTHOR INFORMATION
Corresponding Author
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Notes
(9) Stanforth, S. P. Vinyl and Ary Halides In Comprehensive Organic
Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K.,
Eds.; Elsevier: Oxford, 2005; Vol. 2, pp 561−594.
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS
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Chem. Soc. 1997, 119, 698. (c) Trost, B. M.; McIntosh, M. C.
Tetrahedron Lett. 1997, 38, 3207. (d) Trost, B. M.; Gunzner, J. L.;
Yasukata, T. Tetrahedron Lett. 2001, 42, 3775.
This research was supported by the National Natural Science
Foundation (21302095), Research Fund for the Doctoral
Program of Higher Education (20133221120003), Jiangsu
Provincial NSFC (BK20130924), and Foundation of Jiangsu
Educational Committee (13KJB150019, CXZZ13_0449) of
China. We thank Prof. Jun Ling of Zhejiang University for help
in DFT calculations and Prof. Yi Pan of Nanjing University for
helpful discussions.
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M.; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 2010, 132, 16403.
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133, 740. For a complete list of references, see Supporting
Information.
(13) US 2010/0331370 A1. For a complete list of references, see
Supporting Information.
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(b) Schreiber, S. L. Nature 2009, 457, 153.
DEDICATION
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R.S. would like to dedicate this paper to the memory of his
mentor, Prof. Xian Huang, on the occasion of his 80th birthday.
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dx.doi.org/10.1021/ol500101b | Org. Lett. 2014, 16, 1208−1211