中文
Earlier issues
Announcement
More
Progress in Chemistry 2022, Vol. 34 Issue (6): 1245-1246 DOI: 10.7536/PC220527   Next Articles

Special Issue: 中国化学印记

• Imprint of Chinese Chemistry •

The Synthesis of Thermodynamically Disfavored Disubstituted Cyclohexanes

Shunxi Dong, Xiaohua Liu()   

  1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
  • Online: Published:
  • Contact: Xiaohua Liu
Richhtml ( 44 ) PDF ( 343 ) Cited
Export

EndNote

Ris

BibTeX

Thermodynamically disfavored disubstituted cyclohexanes are synthesized with excellent kinetic stereocontrol from readily available substituted methylenecyclohexanes based on chain-walking catalysis. Control experiments and theoretical calculations suggest that the initial introduction of bulky boron ester substitution away from the ring is crucial to the high diastereoselectivity. This finding opens a new adventure to the application of chain walking catalysis in organic synthesis and provides a ready access to thermodynamically disfavored but biologically important disubstituted cyclohexanes and the derivatives.

[1]
Aldeghi M, Malhotra S, Selwood D L, Chan A W E. Chem. Biol. Drug Des., 2014, 83: 450.

doi: 10.1111/cbdd.12260 pmid: 24472495
[2]
Marson C M. Chem. Soc. Rev., 2011, 40: 5514.

doi: 10.1039/c1cs15119c
[3]
Staszewski M, Nelic D, Jończyk J, Dubiel M, Frank A, Stark H, Bajda M, Jakubik J, Walczyński K. ACS Chem. Neurosci., 2021, 12: 2503.

doi: 10.1021/acschemneuro.1c00237 pmid: 34100603
[4]
Masson G, Lalli C, Benohoud M, Dagousset G, Chem. Soc. Rev., 2013, 42: 902.

doi: 10.1039/C2CS35370A
[5]
Wang W, Ding C, Yin G. Nat. Catal., 2020, 3: 951.

doi: 10.1038/s41929-020-00523-8
[6]
Li Y, Li Y, Shi H, Wei H, Li H, Funes-Ardoiz I, Yin G. Science, 2022, 376: 749.

doi: 10.1126/science.abn9124
[7]
Iwasaki K, Wan K K, Oppedisano A, Crossley S W M, Shenvi R A. J. Am. Chem. Soc., 2014, 136: 1300.

doi: 10.1021/ja412342g pmid: 24428640
[8]
Peters B K Liu, Margarita C, Rabten W, Kerdphon S, Orebom A, Morsch T, Andersson P G. J. Am. Chem. Soc., 2016, 138: 11930.

doi: 10.1021/jacs.6b07291 pmid: 27548029
[9]
Green S A, Vásquez-Céspedes S, Shenvi R A. J. Am. Chem. Soc., 2018, 140: 11317

doi: 10.1021/jacs.8b05868
No related articles found!