Synlett 2024; 35(14): 1609-1612
DOI: 10.1055/s-0043-1763636
synpacts

Methods for the Synthesis of 1-Indanones Containing a β-Quaternary Carbon Center

Shuaishuai Song
,
Wang Zhou
Financial support from the National Natural Science Foundation of China (Grant No. 22071051) and Hunan Normal University is greatly appreciated.


Abstract

This article traces the development of synthetic routes toward 1-indanones containing a β-quaternary carbon center. The recent advancement in the regio- and chemoselective formal (4+1) carbocyclization of chalcones with internal alkynes via rhodium(III) catalysis for the synthesis of 1-indanones is highlighted.



Publication History

Received: 08 October 2023

Accepted after revision: 23 October 2023

Article published online:
30 November 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Patil SA, Patil R, Patil SA. Eur. J. Med. Chem. 2017; 138: 182
  • 2 Marsais F, Levacher V, Papamicael C, Bohn P, Peauger L, Gembus V, Fur NL, Dumartin-Lepine M. WO2014114742A1, 2014
  • 3 Leoni LM, Hamel E, Genini D, Shih H, Carrera CJ, Cottam HB, Carson DA. J. Natl. Cancer Inst. 2000; 92: 217
  • 4 Hao X.-D, Chang J, Qin B.-Y, Zhong C, Chu Z.-B, Huang J, Zhou W.-J, Sun X. Eur. J. Med. Chem. 2015; 102: 26
  • 5 Das S, Dutta A. New J. Chem. 2021; 45: 4545
  • 6 Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE. Angew. Chem. Int. Ed. 2016; 55: 4156
  • 7 Quasdorf KW, Overman LE. Science 2014; 516: 181
  • 8 Fuji K. Chem. Rev. 1993; 93: 2037
  • 9 Shintani R, Hayashi T. Org. Lett. 2005; 7: 2071
  • 10 Shintani R, Takatsu K, Hayashi T. Angew. Chem. Int. Ed. 2007; 46: 3735
  • 11 Matsuda T, Shigeno M, Makino M, Murakami M. Org. Lett. 2006; 8: 3379
  • 12 Seiser T, Cathomen G, Cramer N. Synlett 2010; 11: 1699
  • 13 Sun Y.-L, Wang X.-B, Sun F.-N, Chen Q.-Q, Cao J, Xu Z, Xu L.-W. Angew. Chem. Int. Ed. 2019; 58: 6747
  • 14 Sun F.-N, Yang W.-C, Chen X.-B, Sun Y.-L, Cao J, Xua Z, Xu L.-W. Chem. Sci. 2019; 10: 7579
  • 15 Yang W.-C, Chen X.-B, Song K.-L, Wu B, Gan W.-E, Zheng Z.-J, Cao J, Xu L.-W. Org. Lett. 2021; 23: 1309
  • 16 Xia Y, Lu G, Liu P, Dong G. Nature 2016; 539: 546
  • 17 Xia Y, Wang J, Dong G. Angew. Chem. Int. Ed. 2017; 56: 2376
  • 18 Yu S, Liu S, Lan Y, Wan B, Li X. J. Am. Chem. Soc. 2015; 137: 1623
  • 19 Lou J, Han W, Liu Z, Xiao J. Org. Chem. Front. 2021; 8: 1447
  • 20 Cai S.-L, Yan L, Yang C, Sheng J, Wang X.-S. ACS Catal. 2019; 9: 10299
  • 21 Song S, Lai Y, Tuo Z, Zhong J, Zhou W. Angew. Chem. Int. Ed. 2023; 62: e202305983
  • 22 Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308