Recent Advances in the Catalytic Cycloaddition of 1,n‑Dipolesweb.pkusz.edu.cn › huang › files...
Transcript of Recent Advances in the Catalytic Cycloaddition of 1,n‑Dipolesweb.pkusz.edu.cn › huang › files...
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Recent Advances in the Catalytic Cycloaddition of 1,n-Dipoles
Reporter: XiaoBo
Supervisor: Prof. Huang
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Noncatalytic 1,4-Dipolar Cycloaddition
New York, 1969; p 223.
E. Chem. Ber. 1967, 100, 1094− 1106.
INTRODUCTION
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EXAMPLES:
Donor−Acceptor Cyclobutanes
γ-Methylidene-δ-valerolactones
Vinyl Benzoxazinanones
Allenoates
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Generation of 1,n-Dipoles from D–A Cycloalkanes
Angew. Chem., Int. Ed. Engl. 1980, 19, 813−814.
Chem. Rev. 2003, 103, 1151−1196.
DONOR−ACCEPTOR CYCLOBUTANES
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Lewis Acid-Catalyzed [4 + 2] Cycloadditions of D–A
Cyclobutanes and Aldehydes
J. Am. Chem. Soc. 2009, 131, 14202−14203.
DONOR−ACCEPTOR CYCLOBUTANES
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Stereoselective 1,4-Dipolar Cycloadditions of D–A Cyclobutanes
Org. Lett. 2010, 12, 4732−4735.
Org. Lett. 2011, 13, 1528−1531..
DONOR−ACCEPTOR CYCLOBUTANES
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Synthesis of (±)-Akuammicine via [4 + 2] Cycloaddition
of D–A Cyclobutane
Angew. Chem., Int. Ed. 2017, 56, 3055−3058.
DONOR−ACCEPTOR CYCLOBUTANES
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1,4-Dipolar Cycloadditions of Modified D–A Cyclobutanes Org. Lett. 2010, 12, 4736−4738.
Org. Lett. 2011, 13, 1528−1531.
Chem. Commun. 2014, 50, 1668−1670.
DONOR−ACCEPTOR CYCLOBUTANES
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Generation of 1,4-Dipoles from γ-Methylidene-δ-valerolactones
Chem. Soc. Jpn. 2012, 85, 931−939.
γ-Methylidene-δ-valerolactones
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[4 + 3] Cycloadditions of γ-Methylidene-δ-valerolactones Org. Lett. 2009, 11, 5642−5645.
γ-Methylidene-δ-valerolactones
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[4 + 2] Cycloadditions of γ-Methylidene-δ-valerolactones J. Am. Chem. Soc. 2008, 130, 16174−16175.
J. Am. Chem. Soc.2010, 132, 7508−7513.
Org. Lett. 2012, 14, 2410−2413.
γ-Methylidene-δ-valerolactones
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[4 + 1] Cycloaddition of γ-Methylidene-δ-valerolactones
Chem. Lett. 2009, 38, 204− 205.
γ-Methylidene-δ-valerolactones
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[6 + 3] Cycloadditions of γ-Methylidene-δ-valerolactones Org. Lett. 2009, 11, 5642−5645.
γ-Methylidene-δ-valerolactones
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[4 + 2] Cycloadditions of Vinyl Oxazinanones Angew. Chem., Int. Ed. 2016, 55,2200– 2204
Vinyl Benzoxazinanones
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Palladium(0)-Catalyzed [4 + 2] Cycloaddition of Vinyl
Benzoxazinanones and Isatins Org. Lett. 2017, 19, 3219– 3222
Vinyl Benzoxazinanones
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[4 + 1] Cycloaddition of Vinyl Benzoxazinanones and Sulfur Ylides
Nat. Commun. 2014, 5, 5500– 5510
Vinyl Benzoxazinanones
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1,n-Dipolar Species from Allenoates
Allenoates
Tetrahedron Lett. 1997, 38, 3461– 3464
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Phosphine-Catalyzed [4 + 2] Cycloaddition of Allenoates and Imines
Allenoates
J. Am. Chem. Soc. 2003, 125, 4716– 4717
J. Am. Chem. Soc. 2007, 129, 12632– 12633
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Summary
The use of transition metal, Lewis acid in 1,n-dipolar
cycloaddition triggers the reaction by generating the 1,n-
dipoles and provides the opportunity to achieve regio- and
stereoselective transformations.
The development of atypical 1,n-dipolar cycloadditions will
continue to be a leading area in synthetic chemistry toward
functional cyclic compounds and natural products.
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Thanks a lot.