Page 32 - Read Online

Wu et al. Chem Synth 2023;3:6 https://dx.doi.org/10.20517/cs.2022.42 Page 13 of 17

dithioacetals: diastereoselective synthesis of highly functionalized cyclopenta[b]indoles. Tetrahedron Lett 2020;61:152349. DOI
23. Mao J, Zhang H, Ding XF, Luo X, Deng WP. Synergistic catalysis for asymmetric [3+2] cycloadditions of 2-indolylmethanols with α
, β-unsaturated aldehydes. J Org Chem 2019;84:11186-94. DOI PubMed
24. Tian F, Yang W, Ni T, Zhang J, Deng W. Catalytic asymmetric dipolar cycloadditions of indolyl delocalized metal-allyl species for
the enantioselective synthesis of cyclopenta[b]indoles and pyrrolo[1,2-a]indoles. Sci China Chem 2021;64:34-40. DOI
25. Gao JG, Guan XK, Sun DY, et al. Enantioselective domino reaction of 3-vinylindole and p-quinone methides enabled by chiral
imidodiphosphoric acids: asymmetric synthesis of multisubstituted 3-indolyl cyclopenta[b]indoles. Org Lett 2021;23:4876-81. DOI
PubMed
26. Fan T, Zhang H, Li C, Shen Y, Shi F. The application of N-protected 3-vinylindoles in chiral phosphoric acid-catalyzed [3+2]
cyclization with 3-indolylmethanols: monoactivation of the catalyst to vinyliminium. Adv Synth Catal 2016;358:2017-31. DOI
27. Zhang H, Zhu Z, Fan T, Liang J, Shi F. Intermediate-dependent unusual [4+3], [3+2] and cascade reactions of 3-indolylmethanols:
controllable chemodivergent and stereoselective synthesis of diverse indole derivatives. Adv Synth Catal 2016;358:1259-88. DOI
28. Zhu Z, Shen Y, Sun X, Tao J, Liu J, Shi F. Catalytic asymmetric [3+2] cycloadditions of C-3 unsubstituted 2-indolylmethanols:
regio-, diastereo- and enantioselective construction of the cyclopenta[b]indole framework. Adv Synth Catal 2016;358:3797-808. DOI
29. Xu MM, Wang HQ, Wan Y, Wang SL, Shi F. Enantioselective construction of cyclopenta[b]indoles scaffolds via the catalytic
asymmetric [3+2] cycloaddition of 2-indolylmethanols with p-hydroxystyrenes. J Org Chem 2017;82:10226-33. DOI PubMed
30. Vaidya T, Eisenberg R, Frontier AJ. Catalytic Nazarov cyclization: the state of the art. ChemCatChem 2011;3:1531-48. DOI
31. Shimada N, Stewart C, Tius MA. Asymmetric Nazarov cyclizations. Tetrahedron 2011;67:5851-70. DOI PubMed PMC
32. Tius MA. Allene ether Nazarov cyclization. Chem Soc Rev 2014;43:2979-3002. DOI PubMed
33. Grandi MJ. Nazarov-like cyclization reactions. Org Biomol Chem 2014;12:5331-45. DOI PubMed
34. Wenz DR, Read de Alaniz J. The Nazarov cyclization: a valuable method to synthesize fully substituted carbon stereocenters:
Nazarov cyclization. Eur J Org Chem 2015;2015:23-37. DOI
35. Simeonov SP, Nunes JP, Guerra K, Kurteva VB, Afonso CA. Synthesis of chiral cyclopentenones. Chem Rev 2016;116:5744-893.
DOI PubMed
36. Vinogradov MG, Turova OV, Zlotin SG. Nazarov reaction: current trends and recent advances in the synthesis of natural compounds
and their analogs. Org Biomol Chem 2017;15:8245-69. DOI PubMed
37. Malona JA, Colbourne JM, Frontier AJ. A general method for the catalytic Nazarov cyclization of heteroaromatic compounds. Org
Lett 2006;8:5661-4. DOI PubMed
38. Davies J, Leonori D. The first calcium-catalysed Nazarov cyclisation. Chem Commun 2014;50:15171-4. DOI PubMed
39. Raja S, Nakajima M, Rueping M. Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-
heterocycles. Angew Chem Int Ed Engl 2015;54:2762-5. DOI PubMed
40. Wang GP, Chen MQ, Zhu SF, Zhou QL. Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis
acids and chiral Brønsted acids. Chem Sci 2017;8:7197-202. DOI PubMed PMC
41. Rinaldi A, Petrović M, Magnolfi S, Scarpi D, Occhiato EG. Pentannulation reaction by tandem gold(I)-catalyzed propargyl Claisen
rearrangement/Nazarov cyclization of enynyl vinyl ethers. Org Lett 2018;20:4713-7. DOI PubMed
42. Dhiman S, Ramasastry SS. One-pot relay gold(I) and brønsted acid catalysis: cyclopenta[b]annulation of indoles via
hydroamination/Nazarov-type cyclization cascade of enynols. Org Lett 2015;17:5116-9. DOI PubMed
43. Wang Z, Xu X, Gu Z, et al. Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-
quinoline]s. Chem Commun 2016;52:2811-4. DOI PubMed PMC
44. Scarpi D, Petrović M, Fiser B, Gómez-Bengoa E, Occhiato EG. Construction of Cyclopenta[b]indol-1-ones by a tandem gold(I)-
catalyzed rearrangement/Nazarov reaction and application to the synthesis of bruceolline H. Org Lett 2016;18:3922-5. DOI PubMed
45. Wang C, Wu J, Li C, Li L, Mei G, Shi F. Design of C3-alkenyl-substituted 2-indolylmethanols for catalytic asymmetric interrupted
Nazarov-type cyclization. Adv Synth Catal 2018;360:846-51. DOI
46. Wu JL, Wang JY, Wu P, Wang JR, Mei GJ, Shi F. Diastereo- and enantioselective construction of chiral cyclopenta[b]indole
framework via a catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols. Org Chem Front 2018;5:1436-45.
DOI
47. Wang JY, Wu P, Wu JL, Mei GJ, Shi F. Chemodivergent tandem cyclizations of 2-indolylmethanols with tryptophols: C-N versus C-
C bond formation. J Org Chem 2018;83:5931-46. DOI PubMed
48. Rueping M, Ieawsuwan W, Antonchick AP, Nachtsheim BJ. Chiral Brønsted acids in the catalytic asymmetric Nazarov cyclization--
the first enantioselective organocatalytic electrocyclic reaction. Angew Chem Int Ed Engl 2007;46:2097-100. DOI PubMed
49. Rueping M, Ieawsuwan W. A catalytic asymmetric electrocyclization-protonation reaction. Adv Synth Catal 2009;351:78-84. DOI
50. Basak AK, Shimada N, Bow WF, Vicic DA, Tius MA. An organocatalytic asymmetric Nazarov cyclization. J Am Chem Soc
2010;132:8266-7. DOI PubMed PMC
51. Jolit A, Walleser PM, Yap GP, Tius MA. Catalytic enantioselective Nazarov cyclization: construction of vicinal all-carbon-atom
quaternary stereocenters. Angew Chem Int Ed Engl 2014;53:6180-3. DOI PubMed
52. Yang BM, Cai PJ, Tu YQ, et al. Organocatalytic asymmetric tandem Nazarov cyclization/semipinacol rearrangement: rapid
construction of chiral spiro[4.4]nonane-1,6-diones. J Am Chem Soc 2015;137:8344-7. DOI PubMed
53. Süsse L, Vogler M, Mewald M, Kemper B, Irran E, Oestreich M. Enantioselective Nazarov cyclizations catalyzed by an axial chiral
C F -substituted boron Lewis acid. Angew Chem Int Ed Engl 2018;57:11441-4. DOI PubMed
6 5