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Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes.
J Org Chem. 2023 Jun 16; 88(12):7703-7711.JO

Abstract

Dithia[5]helicenes and helically chiral thia[6]helicenes were synthesized in high yields via a cationic Rh-catalyzed intramolecular [2 + 2 + 2] cycloaddition of triynes bearing sulfur-containing 1,6-diynes. Thia[6]helicene could be obtained with a high enantiomeric excess of P-isomers by using (S)-SEGPHOS as a chiral ligand. This protocol is the first example of the synthesis of thiahelicenes via [2 + 2 + 2] cycloaddition and can also be used for the asymmetric construction of an aza[6]helical skeleton.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Nishibe S
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Kishi T
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Ito M
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Shibata T
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.

MeSH

Cycloaddition ReactionRhodiumStereoisomerismPolycyclic Compounds

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36753708

Citation

Nishibe, Shun, et al. "Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes Via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes." The Journal of Organic Chemistry, vol. 88, no. 12, 2023, pp. 7703-7711.
Nishibe S, Kishi T, Ito M, et al. Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes. J Org Chem. 2023;88(12):7703-7711.
Nishibe, S., Kishi, T., Ito, M., & Shibata, T. (2023). Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes. The Journal of Organic Chemistry, 88(12), 7703-7711. https://doi.org/10.1021/acs.joc.2c02466
Nishibe S, et al. Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes Via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes. J Org Chem. 2023 Jun 16;88(12):7703-7711. PubMed PMID: 36753708.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of Dithia[5]helicenes and Enantioselective Synthesis of Helically Chiral Thia[6]helicenes via Rh-Catalyzed Intramolecular [2 + 2 + 2] Cycloaddition of Triynes. AU - Nishibe,Shun, AU - Kishi,Taichi, AU - Ito,Mamoru, AU - Shibata,Takanori, Y1 - 2023/02/08/ PY - 2023/2/9/medline PY - 2023/2/9/pubmed PY - 2023/2/8/entrez SP - 7703 EP - 7711 JF - The Journal of organic chemistry JO - J Org Chem VL - 88 IS - 12 N2 - Dithia[5]helicenes and helically chiral thia[6]helicenes were synthesized in high yields via a cationic Rh-catalyzed intramolecular [2 + 2 + 2] cycloaddition of triynes bearing sulfur-containing 1,6-diynes. Thia[6]helicene could be obtained with a high enantiomeric excess of P-isomers by using (S)-SEGPHOS as a chiral ligand. This protocol is the first example of the synthesis of thiahelicenes via [2 + 2 + 2] cycloaddition and can also be used for the asymmetric construction of an aza[6]helical skeleton. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/36753708/Synthesis_of_Dithia[5]helicenes_and_Enantioselective_Synthesis_of_Helically_Chiral_Thia[6]helicenes_via_Rh_Catalyzed_Intramolecular_[2_+_2_+_2]_Cycloaddition_of_Triynes_ DB - PRIME DP - Unbound Medicine ER -