Strain release – an old tool for new transformations

Joanna Turkowska; Jakub Durka; Dorota Gryko

doi:10.1039/d0cc01771j

journal article Jan 01, 2020

Strain release – an old tool for new transformations

Joanna Turkowska

Jakub Durka

Dorota Gryko

Chemical Communications Vol. 56 No. 43 pp. 5718-5734 · Royal Society of Chemistry (RSC)

View at Publisher Save 10.1039/d0cc01771j

Abstract

This Feature Article provides an overview of research advances in the chemistry of spring-loaded molecules, focusing mainly on strain-release transformations.

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References

88

[1]

Von Baeyer Ber. Dtsch. Chem. Ges. (1885) 10.1002/cber.18850180296

[2]

Wiberg Angew. Chem., Int. Ed. Engl. (1986) 10.1002/anie.198603121

[3]

Levin Chem. Rev. (2000) 10.1021/cr990094z

[4]

Delia Org. Prep. Proced. Int. (1996) 10.1080/00304949609356550

[5]

Bartnik Synlett (1997) 10.1055/s-1997-1520

[6]

S. Hoz , in The Chemistry of the Cyclopropyl Group , ed. Z. Rappoport , Wiley , New York , 1987 , vol. 1, pp. 1121–1191

[7]

Jamieson J. Chem. Soc., Perkin Trans. 2 (1980) 10.1039/p29800001366

[8]

Wiberg J. Am. Chem. Soc. (1990) 10.1021/ja00162a022

[9]

Gianatassio Science (2016) 10.1126/science.aad6252

[10]

Click Chemistry: Diverse Chemical Function from a Few Good Reactions

Hartmuth C. Kolb, M. G. Finn, K. Barry Sharpless

Angewandte Chemie International Edition 2001 10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.0.co;2-5

[11]

Boström Nat. Rev. Drug Discovery (2018) 10.1038/nrd.2018.116

[12]

Polo J. Comput. Chem. (2007) 10.1002/jcc.20615

[13]

Ioffe Bull. Acad. Sci. USSR, Div. Chem. Sci. (1988) 10.1007/bf00962498

[14]

Ring strain energies: substituted rings, norbornanes, norbornenes and norbornadienes

Peter R. Khoury, John D. Goddard, William Tam

Tetrahedron 2004 10.1016/j.tet.2004.06.100

[15]

Smith J. Comput. Chem. (2013) 10.1002/jcc.23165

[16]

Seiler Helv. Chim. Acta (1990) 10.1002/hlca.19900730603

[17]

Gassman J. Am. Chem. Soc. (1983) 10.1021/ja00356a025

[18]

Suenram J. Chem. Phys. (1972) 10.1063/1.1677787

[19]

Dilmaç Angew. Chem., Int. Ed. (2017) 10.1002/anie.201603951

[20]

Kanazawa Synlett (2019) 10.1055/s-0037-1610314

[21]

Locke Chem. – Eur. J. (2019) 10.1002/chem.201804225

[22]

Ma Asian J. Org. Chem. (2020) 10.1002/ajoc.201900589

[23]

Fawcett Pure Appl. Chem. (2019) 10.1515/pac-2019-1007

[24]

Wiberg React. Intermed. Chem. (2004)

[25]

Wu Angew. Chem., Int. Ed. (2009) 10.1002/anie.200804965

[26]

Galasso Chem. Phys. Lett. (1994) 10.1016/0009-2614(94)01174-5

[27]

Wiberg Acc. Chem. Res. (1984) 10.1021/ar00107a001

[28]

Bauld J. Am. Chem. Soc. (1977) 10.1021/ja00467a003

[29]

Baric Theor. Chem. Acc. (2005) 10.1007/s00214-005-0664-x

[30]

Schulman J. Am. Chem. Soc. (1970) 10.1021/ja00725a053

[31]

Newton J. Am. Chem. Soc. (1972) 10.1021/ja00758a015

[32]

Whitman J. Am. Chem. Soc. (1972) 10.1021/ja00759a016

[33]

Bartnik J. Chem. Soc., Chem. Commun. (1993) 10.1039/c39930000148

[34]

Bohn J. Am. Chem. Soc. (1970) 10.1021/ja00725a010

[35]

Lampman Org. Synth. (1971) 10.15227/orgsyn.051.0055

[36]

Gaoni Tetrahedron Lett. (1988) 10.1016/s0040-4039(00)80361-5

[37]

Gaoni Org. Prep. Proced. Int. (1995) 10.1080/00304949509458453

[38]

Hoz Tetrahedron (1979) 10.1016/0040-4020(79)80110-6

[39]

Gaoni Tetrahedron Lett. (1982) 10.1016/s0040-4039(00)85801-3

[40]

Gaoni Tetrahedron (1989) 10.1016/s0040-4020(01)80112-5

[41]

Gaoni J. Org. Chem. (1985) 10.1021/jo00216a027

[42]

Gaoni J. Org. Chem. (1985) 10.1021/jo00216a028

[43]

Wiberg J. Am. Chem. Soc. (1994) 10.1021/ja00105a046

[44]

Rehm Eur. J. Org. Chem. (1999) 10.1002/(sici)1099-0690(199909)1999:9<2079::aid-ejoc2079>3.0.co;2-d

[45]

Panish J. Am. Chem. Soc. (2013) 10.1021/ja403811t

[46]

Gianatassio Org. Lett. (2019) 10.1021/acs.orglett.9b00321

[47]

Makarov Angew. Chem., Int. Ed. (2017) 10.1002/anie.201706799

[48]

Messner Eur. J. Org. Chem. (2000) 10.1002/1099-0690(200004)2000:7<1137::aid-ejoc1137>3.0.co;2-2

[49]

Yu Angew. Chem., Int. Ed. (2020) 10.1002/anie.201914875

[50]

Pellicciari J. Med. Chem. (1996) 10.1021/jm960254o

Showing 50 of 88 references

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Metrics

237

Citations

88

References

Details

Published: Jan 01, 2020
Vol/Issue: 56(43)
Pages: 5718-5734
License: View

Authors

J

Joanna Turkowska

Institute of Organic Chemistry Polish Academy of Sciences; Warsaw 01-224; Poland

J

Jakub Durka

Institute of Organic Chemistry Polish Academy of Sciences; Warsaw 01-224; Poland; Department of Chemistry; Warsaw University of Technology

D

Dorota Gryko

Institute of Organic Chemistry Polish Academy of Sciences; Warsaw 01-224; Poland

Funding

Fundacja na rzecz Nauki Polskiej Award: FNP TEAM POIR.04.04.00–00–4232/17–00

Cite This Article

Joanna Turkowska, Jakub Durka, Dorota Gryko (2020). Strain release – an old tool for new transformations. Chemical Communications, 56(43), 5718-5734. https://doi.org/10.1039/d0cc01771j

Strain release – an old tool for new transformations

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