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...
Recent Advances in the Catalytic Cycloaddition of 1,n-Dipoles
Reporter: XiaoBo
Supervisor: Prof. Huang
Noncatalytic 1,4-Dipolar Cycloaddition
New York, 1969; p 223.
E. Chem. Ber. 1967, 100, 1094− 1106.
INTRODUCTION
EXAMPLES:
Donor−Acceptor Cyclobutanes
γ-Methylidene-δ-valerolactones
Vinyl Benzoxazinanones
Allenoates
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
Lewis Acid-Catalyzed [4 + 2] Cycloadditions of D–A
Cyclobutanes and Aldehydes
J. Am. Chem. Soc. 2009, 131, 14202−14203.
DONOR−ACCEPTOR CYCLOBUTANES
Stereoselective 1,4-Dipolar Cycloadditions of D–A Cyclobutanes
Org. Lett. 2010, 12, 4732−4735.
Org. Lett. 2011, 13, 1528−1531..
DONOR−ACCEPTOR CYCLOBUTANES
Synthesis of (±)-Akuammicine via [4 + 2] Cycloaddition
of D–A Cyclobutane
Angew. Chem., Int. Ed. 2017, 56, 3055−3058.
DONOR−ACCEPTOR CYCLOBUTANES
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
Generation of 1,4-Dipoles from γ-Methylidene-δ-valerolactones
Chem. Soc. Jpn. 2012, 85, 931−939.
γ-Methylidene-δ-valerolactones
[4 + 3] Cycloadditions of γ-Methylidene-δ-valerolactones Org. Lett. 2009, 11, 5642−5645.
γ-Methylidene-δ-valerolactones
[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
[4 + 1] Cycloaddition of γ-Methylidene-δ-valerolactones
Chem. Lett. 2009, 38, 204− 205.
γ-Methylidene-δ-valerolactones
[6 + 3] Cycloadditions of γ-Methylidene-δ-valerolactones Org. Lett. 2009, 11, 5642−5645.
γ-Methylidene-δ-valerolactones
[4 + 2] Cycloadditions of Vinyl Oxazinanones Angew. Chem., Int. Ed. 2016, 55,2200– 2204
Vinyl Benzoxazinanones
Palladium(0)-Catalyzed [4 + 2] Cycloaddition of Vinyl
Benzoxazinanones and Isatins Org. Lett. 2017, 19, 3219– 3222
Vinyl Benzoxazinanones
[4 + 1] Cycloaddition of Vinyl Benzoxazinanones and Sulfur Ylides
Nat. Commun. 2014, 5, 5500– 5510
Vinyl Benzoxazinanones
1,n-Dipolar Species from Allenoates
Allenoates
Tetrahedron Lett. 1997, 38, 3461– 3464
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
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.
Thanks a lot.