Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes

Elena Braconi; Alissa C. Götzinger; Nicolai Cramer

doi:10.1021/jacs.0c09486

journal article Nov 11, 2020

Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes

Elena Braconi

Alissa C. Götzinger Nicolai Cramer

Journal of the American Chemical Society Vol. 142 No. 47 pp. 19819-19824 · American Chemical Society (ACS)

View at Publisher Save 10.1021/jacs.0c09486

Topics

No keywords indexed for this article. Browse by subject →

References

73

[1]

10.1016/s0040-4039(00)95101-3

[2]

10.1021/ja00738a045

[3]

10.1021/ja00785a054

[4]

aGranier, T.; Bajgrowicz, J. A.; Hanhart, A. Cyclooct-(En)-yl Derivatives for Use as Fragrances. US Patent 7888309, 2011.

[5]

10.1021/ef5027746

[6]

10.1002/pola.28695

[7]

10.1002/anie.200703612

[8]

10.1021/acscatal.6b02495

[9]

10.1021/ol0476063

[10]

10.1016/j.tetasy.2005.02.022

[11]

10.1021/ol0524914

[12]

10.1021/om050093z

[13]

10.1021/ar00064a001

[14]

10.1002/1099-0690(200009)2000:18<3117::aid-ejoc3117>3.0.co;2-5

[15]

10.1021/jm4017625

[16]

10.1021/ar960101v

[17]

10.1021/cr990407q

[18]

10.1002/1521-3773(20000616)39:12<2073::aid-anie2073>3.0.co;2-0

[19]

Blanchard N. (2010)

[20]

10.1126/science.aaf6742

[21]

10.1021/jacs.7b13260

[22]

10.1038/nchembio.1130

[23]

10.1039/d0sc00568a

[24]

10.1016/0040-4020(95)01077-7

[25]

10.1002/asia.200900712

[26]

10.1021/ja00225a055

[27]

10.1021/ja00242a065

[28]

10.1002/ange.19550671610

[29]

10.1002/jlac.19697270119

[30]

10.1039/jr9540001931

[31]

Oenbrink G. (2009)

[32]

10.1016/0031-6458(77)90059-4

[33]

10.1016/s0065-3055(08)60633-4

[34]

10.1016/s0040-4020(01)97949-9

[35]

10.1016/0022-328x(85)87379-4

[36]

10.1021/cr040664h

[37]

10.1021/cr500425u

[38]

10.1021/acscentsci.6b00272

[39]

10.1021/acs.chemrev.6b00772

[40]

Plietker B. (2008) 10.1002/9783527623273

[41]

Bauer E. B. (2015)

[42]

Nakamura E. (2014)

[43]

10.1007/s41061-016-0059-6

[44]

10.1002/anie.198507811

[45]

10.1002/anie.199203051

[46]

10.1021/jacs.8b00245

[47]

Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes

C. Rose Kennedy, Hongyu Zhong, Rachel L. Macaulay et al.

Journal of the American Chemical Society 10.1021/jacs.9b02443

[48]

10.1021/acs.organomet.6b00474

[49]

aChirik, P. J.; Tondreau, A. M.; Delis, G. P. J.; Lewis, K. M.; Weller, K. J.; Nye, S. A. In-situ activation of metal complexes containing terdentate nitrogen ligands used as hydrosilylation catalysts. US Patent 8765987B2, 2010, and US Patent 2012/0130106, 2012.

[50]

10.1039/c1cc14622j

Showing 50 of 73 references

Cited By

41

Synthesis and Analysis of the Structure of a Trinuclear Complex of Cobalt(II) Benzoate with 1,4-Diaza-1,3-Butadiene Ligand Mes-DAD

V. A. Bushuev, D. S. Yambulatov · 2025

Journal of Structural Chemistry

Diastereoselective Construction of Eight-Membered Carbocycles through Palladium-Catalyzed C(sp3)–H Functionalization

Bin Wan, Zhicheng Lu · 2021

Organic Letters

Metrics

41

Citations

73

References

Details

Published: Nov 11, 2020
Vol/Issue: 142(47)
Pages: 19819-19824
License: View

Authors

E

Elena Braconi

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland

A

Alissa C. Götzinger

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland

N

Nicolai Cramer

Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland

Funding

Deutsche Forschungsgemeinschaft

Cite This Article

Elena Braconi, Alissa C. Götzinger, Nicolai Cramer (2020). Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes. Journal of the American Chemical Society, 142(47), 19819-19824. https://doi.org/10.1021/jacs.0c09486

Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes

You May Also Like