Advances in the synthetic methods of bicyclo1.1.1pentane derivatives

HUANG Yu; ZHANG Yinsheng

doi:10.11665/j.issn.1000-5048.20220202

Journal of China Pharmaceutical University > 2022 > 53(2): 137-145. > DOI: 10.11665/j.issn.1000-5048.20220202

HUANG Yu, ZHANG Yinsheng. Advances in the synthetic methods of bicyclo[1.1.1]pentane derivatives[J]. Journal of China Pharmaceutical University, 2022, 53(2): 137-145. DOI: 10.11665/j.issn.1000-5048.20220202

Citation:

PDF (1439 KB)

Advances in the synthetic methods of bicyclo[1.1.1]pentane derivatives

Jiangsu Key Laboratory of Targeted Antiviral Research, Chia Tai Tianqing Pharmaceutical Group, Nanjing 211100, China

Funds: This study was supported by the Program of Jiangsu Key Laboratory of Targeted Antiviral Research ([2019] No.1627)

More Information

Received Date: October 31, 2021
Revised Date: December 21, 2021

Graphical Abstract

Abstract

Abstract

Bicyclo [1.1.1] pentane (BCP) is a kind of bridged ring skeleton with a three-dimensional structure. As a bioisostere of benzene ring, tert-butyl and alkyne, it has been widely used in the field of medicinal chemistry.With the expansion of its application, the synthesis of BCP and its derivatives has become an increasingly attractive research hotspot for scientists.Based on this, the present article summarizes the main synthetic strategies and methods of BCP derivatives, in the hope of providing some reference for drug discovery researchers and some insight for new synthetic methods of such compounds.
- bcyclo [1.1.1] pentane (BCP),
- synthetic methods,
- advances

FullText(HTML)

References (35)

References

[1]	pentane （BCP） in drug design ［J］. J China Pharm Univ （中国药科大学学报），2022，53（1）：1-9.
[2]	Bauer MR，di Fruscia P，Lucas SCC，et al. Put a ring on it：application of small aliphatic rings in medicinal chemistry［J］. RSC Med Chem，2021，12（4）：448-471.
[3]	Wiberg KB，Connor DS，Lampman GM. The reaction of 3-bromocyclobutane-1-methyl bromide with sodium：bicyclo ［1.1.1］ pentane［J］. Tetrahedron Lett，1964，5（10）：531-534.
[4]	Wiberg KB，Lampman GM，Ciula RP，et al. Bicyclo ［1.1.0］butane［J］. Tetrahedron，1965，21（10）：2749-2769.
[5]	Applequist DE，Renken TL，Wheeler JW. Polar substituent effects in 1，3-disubstituted bicyclo ［1.1.1］ pentanes［J］. J Org Chem，1982，47（25）：4985-4995.
[6]	Ma XS，Sloman DL，Han YX，et al. A selective synthesis of 2，2-difluorobicyclo ［1.1.1］ pentane analogues："BCP-F 2"［J］. Org Lett，2019，21（18）：7199-7203.
[7]	Bychek RM，Hutskalova V，Bas YP，et al. Difluoro-substituted bicyclo［1.1.1］pentanes for medicinal chemistry：design，synthesis，and characterization［J］. J Org Chem，2019，84（23）：15106-15117.
[8]	Gianatassio R，Lopchuk JM，Wang J，et al. Organic chemistry. strain-release amination［J］. Science，2016，351（6270）：241-246.
[9]	Sterling AJ，Dürr AB，Smith RC，et al. Rationalizing the diverse reactivity of ［1.1.1］ propellane through σ-π-delocalization［J］. Chem Sci，2020，11（19）：4895-4903.
[10]	Wiberg KB，Walker FH. ［1.1.1］propellane［J］. J Am Chem Soc，1982，104（19）：5239-5240.
[11]	Semmler K，Szeimies G，Belzner J. Tetracyclo［5.1.0.01，6.02，7］octane，a ［1.1.1］ propellane derivative，and a new route to the parent hydrocarbon［J］. J Am Chem Soc，1985，107（22）：6410-6411.
[12]	Belzner J，Bunz U，Semmler K，et al. Concerning the synthesis of［1.1.1］ propellane［J］. Chem Ber，1989，122（2）：397-398.
[13]	Caputo DFJ，Arroniz C，Dürr AB，et al. Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo［1.1.1］ pentanes［J］. Chem Sci，2018，9（23）：5295-5300.
[14]	Nugent J，Arroniz C，Shire BR，et al. A general route to bicyclo［1.1.1］ pentanes through photoredox catalysis［J］. ACS Catal，2019，9（10）：9568-9574.
[15]	Nugent J，Shire BR，Caputo DFJ，et al. Synthesis of all-carbon disubstituted bicyclo ［1.1.1］pentanes by iron-catalyzed kumada cross-coupling［J］. Angew Chem Int Ed Engl，2020，59（29）：11866-11870.
[16]	Shin S，Lee S，Choi W，et al. Visible-light-induced 1，3-aminopyridylation of ［1.1.1］ propellane with N-aminopyridinium salts［J］. Angew Chem Int Ed，2021，60（14）：7873-7879.
[17]	Wong MLJ，Sterling AJ，Mousseau JJ，et al. Direct catalytic asymmetric synthesis of α-chiral bicyclo ［1.1.1］pentanes［J］. Nat Commun，2021，12（1）：1644.
[18]	Kondo M，Kanazawa J，Ichikawa T，et al. Silaboration of ［1.1.1］propellane：a storable feedstock for bicyclo［1.1.1］pentane derivatives［J］. Angew Chem Int Ed Engl，2020，59（5）：1970-1974.
[19]	Kanazawa J，Maeda K，Uchiyama M. Radical multicomponent carboamination of ［1.1.1］propellane［J］. J Am Chem Soc，2017，139（49）：17791-17794.
[20]	Kim JH，Ruffoni A，Al-Faiyz YSS，et al. Divergent strain-release amino-functionalization of ［1.1.1］ propellane with electrophilic nitrogen-radicals［J］. Angew Chem Int Ed Engl，2020，59（21）：8225-8231.
[21]	Zhang XH，Smith RT，Le C，et al. Copper-mediated synthesis of drug-like bicyclopentanes［J］. Nature，2020，580（7802）：220-226.
[22]	Wiberg KB，Waddell ST. Reactions of ［1.1.1］ propellane［J］. J Am Chem Soc，1990，112（6）：2194-2216.
[23]	Della EW，Taylor DK，Tsanaktsidis J. Unusual bridgehead reactivity：formation of ［1.1.1］ propellane by 1，3-dehydrobromination of 1-bromobicyclo ［1.1.1］ pentane［J］. Tetrahedron Lett，1990，31（36）：5219-5220.
[24]	Bunz U，Szeimies G. Reduction of ［1.1.1］ propellane with lithium 4，4''-di-t-butylbiphenyl：bicyclo ［1.1.1］ pent-1，3-diyldilithium［J］. Tetrahedron Lett，1990，31（5）：651-652.
[25]	Messner M，Kozhushkov SI，de Meijere A. Nickel- and palladium-catalyzed cross-coupling reactions at the bridgehead of bicyclo［1.1.1］pentane derivatives — A convenient access to liquid crystalline compounds containing bicyclo ［1.1.1］ pentane moieties［J］. Eur J Org Chem，2000，2000（7）：1137-1155.
[26]	Makarov IS，Brocklehurst CE，Karaghiosoff K，et al. Synthesis of bicyclo ［1.1.1］ pentane bioisosteres of internal alkynes and para-disubstituted benzenes from ［1.1.1］ propellane［J］. Angew Chem Int Ed Engl，2017，56（41）：12774-12777.
[27]	Yu SJ，Jing CC，Noble A，et al. Iridium-catalyzed enantioselective synthesis of α-chiral bicyclo ［1.1.1］ pentanes by 1，3-difunctionalization of ［1.1.1］ propellane［J］. Org Lett，2020，22（14）：5650-5655.
[28]	Lopchuk JM，Fjelbye K，Kawamata Y，et al. Strain-release heteroatom functionalization：development，scope，and stereospecificity［J］. J Am Chem Soc，2017，139（8）：3209-3226.
[29]	Shelp RA，Walsh PJ. Synthesis of BCP benzylamines from 2-azaallyl anions and ［1.1.1］propellane［J］. Angew Chem Int Ed Engl，2018，57（48）：15857-15861.
[30]	Shelp RA，Ciro A，Pu YG，et al. Strain-release 2-azaallyl anion addition/borylation of ［1.1.1］propellane：synthesis and functionalization of benzylamine bicyclo［1.1.1］pentyl boronates［J］. Chem Sci，2021，12（20）：7066-7072.
[31]	Wiberg KB，McMurdie N. Formation and reactions of bicyclo［1.1.1］pentyl-1 cations［J］. J Am Chem Soc，1994，116（26）：11990-11998.
[32]	Garlets ZJ，Sanders JN，Malik H，et al. Enantioselective C-H functionalization of bicyclo［1.1.1］pentanes［J］. Nat Catal，2020，3（4）：351-357.
[33]	Zhao JX，Chang Y，Elleraas J，et al. 1，2-Difunctionalized Bicyclo［1.1.1］pentanes：long sought after bioisosteres for ortho/meta-substituted arenes［J］. ChemRxiv，2020. https：//doi.org/10. 26434/chemrxiv.13120283.v1.
[34]	Ma XS，Han YX，Bennett DJ. Selective synthesis of 1-dialkylamino-2-alkylbicyclo-［1.1.1］pentanes［J］. Org Lett，2020，22（22）：9133-9138.
[35]	Yang YY，Tsien J，Hughes J，et al. Synthesis of multi-substituted bicycloalkyl boronates：an intramolecular coupling approach to alkyl bioisosteres［J］. ChemRxiv，2021. https：//doi.org/ 10.26434/CHEMRXIV.13724827.V1.

Cited By

Get Citation

PDF

XML

Article views (438) PDF downloads (855)

Turn off MathJax

Article Contents

Abstract

References

Advances in the synthetic methods of bicyclo[1.1.1]pentane derivatives

Abstract

References

Catalog

Export File

Citation

Format

Content