One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization.
J Org Chem. 2020 Feb 21; 85(4):2438-2455.JO

Abstract

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.

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Authors+Show Affiliations

Li Q

Liu J

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 354 Fenglin Lu , Shanghai 200032 , People's Republic of China.

Wei Y

Shi M

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering , East China University of Science and Technology , 130 Mei Long Road , Shanghai 200237 , People's Republic of China. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 354 Fenglin Lu , Shanghai 200032 , People's Republic of China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31876157

Citation

Li, Quanzhe, et al. "One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives Via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization." The Journal of Organic Chemistry, vol. 85, no. 4, 2020, pp. 2438-2455.

Li Q, Liu J, Wei Y, et al. One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization. J Org Chem. 2020;85(4):2438-2455.

Li, Q., Liu, J., Wei, Y., & Shi, M. (2020). One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization. The Journal of Organic Chemistry, 85(4), 2438-2455. https://doi.org/10.1021/acs.joc.9b03126

Li Q, et al. One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives Via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization. J Org Chem. 2020 Feb 21;85(4):2438-2455. PubMed PMID: 31876157.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization. AU - Li,Quanzhe, AU - Liu,Jiaxin, AU - Wei,Yin, AU - Shi,Min, Y1 - 2020/01/08/ PY - 2019/12/27/pubmed PY - 2019/12/27/medline PY - 2019/12/27/entrez SP - 2438 EP - 2455 JF - The Journal of organic chemistry JO - J Org Chem VL - 85 IS - 4 N2 - A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/31876157/One_Pot_Synthesis_of_Spirocyclopenta[a]indene_Derivatives_via_a_Cascade_Ring_Expansion_and_Intramolecular_Friedel_Crafts_Type_Cyclization_ DB - PRIME DP - Unbound Medicine ER -

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One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization.J Org Chem. 2020 Feb 21; 85(4):2438-2455.JO