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Pathway economy in cyclization of 1,n-enynes
- Hezhen Han,
- Wenjie Mao,
- Bin Lin,
- Maosheng Cheng,
- Lu Yang and
- Yongxiang Liu
Beilstein J. Org. Chem. 2025, 21, 2260–2282, doi:10.3762/bjoc.21.173
- synthesis; 1,n-enynes; pathway economy; small-molecule skeletons; Introduction As organic synthesis concepts continue to evolve, economical synthesis remains a foundational principle for synthetic chemists [1][2][3][4][5][6][7]. The essence of economical synthesis lies in the conservation of materials and
Graphical Abstract
Scheme 1: Economical synthesis and pathway economy.
Scheme 2: Au(I)-catalyzed cascade cyclization paths of 1,5-enynes.
Scheme 3: Au(I)-catalyzed cyclization paths of 1,7-enynes.
Scheme 4: I2/TBHP-mediated radical cycloisomerization paths of 1,n-enyne.
Scheme 5: Au(I)-catalyzed cycloisomerization paths of 3-allyloxy-1,6-diynes.
Scheme 6: Pd(II)-catalyzed cycloisomerization paths of 2-alkynylbenzoate-cyclohexadienone.
Scheme 7: Stereoselective cyclization of 1,5-enynes.
Scheme 8: Substituent-controlled cycloisomerization of propargyl vinyl ethers.
Scheme 9: Au(I)-catalyzed pathway-controlled domino cyclization of 1,2-diphenylethynes.
Scheme 10: Au(I)-catalyzed tandem cyclo-isomerization of tryptamine-N-ethynylpropiolamide.
Scheme 11: Au(I)-catalyzed tunable cyclization of 1,6-cyclohexenylalkyne.
Scheme 12: Substituent-controlled 7-exo- and 8-endo-dig-selective cyclization of 2-propargylaminobiphenyl deri...
Scheme 13: BiCl3-catalyzed cycloisomerization of tryptamine-ynamide derivatives.
Scheme 14: Au(I)-mediated substituent-controlled cycloisomerization of 1,6-enynes.
Scheme 15: Ligand-controlled regioselective cyclization of 1,6-enynes.
Scheme 16: Ligand-dependent cycloisomerization of 1,7-enyne esters.
Scheme 17: Ligand-controlled cycloisomerization of 1,5-enynes.
Scheme 18: Ligand-controlled cyclization strategy of alkynylamide tethered alkylidenecyclopropanes.
Scheme 19: Ag(I)-mediated pathway-controlled cycloisomerization of tryptamine-ynamides.
Scheme 20: Gold-catalyzed cycloisomerization of indoles with alkynes.
Scheme 21: Catalyst-dependent cycloisomerization of dienol silyl ethers.
Scheme 22: Cycloisomerization of aromatic enynes governed by catalyst.
Scheme 23: Catalyst-dependent 1,2-migration in cyclization of 1-(indol-2-yl)-3-alkyn-1-ols.
Scheme 24: Gold-catalyzed cycloisomerization of N-propargyl-N-vinyl sulfonamides.
Scheme 25: Gold(I)-mediated enantioselective cycloisomerizations of ortho-(alkynyl)styrenes.
Scheme 26: Catalyst-controlled intramolecular cyclization of 1,7-enynes.
Scheme 27: Brønsted acid-catalyzed cycloisomerizations of tryptamine ynamides.
Scheme 28: Catalyst-controlled cyclization of indolyl homopropargyl amides.
Scheme 29: Angle strain-dominated 6-endo-trig cyclization of propargyl vinyl ethers.
Scheme 30: Angle strain-controlled cycloisomerization of alkyn-tethered indoles.
Scheme 31: Geometrical isomeration-dependent cycloisomerization of 1,3-dien-5-ynes.
Scheme 32: Temperature-controlled cyclization of 1,7-enynes.
Scheme 33: Cycloisomerizations of n-(o-ethynylaryl)acrylamides through temperature modulation.
Scheme 34: Temperature-controlled boracyclization of biphenyl-embedded 1,3,5-trien-7-ynes.
