Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E-H Bonds.
DFT calculations
carbene insertion
diene ligands
rhodium complexes
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
16 Aug 2021
16 Aug 2021
Historique:
revised:
28
05
2021
received:
15
04
2021
pubmed:
1
6
2021
medline:
1
6
2021
entrez:
31
5
2021
Statut:
ppublish
Résumé
A new method for the synthesis of chiral diene rhodium catalysts is introduced. The readily available racemic tetrafluorobenzobarrelene complexes [(R
Identifiants
pubmed: 34057807
doi: 10.1002/anie.202105179
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
18712-18720Subventions
Organisme : Russian Science Foundation
ID : 17-73-20144
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. Int. Ed. 2008, 47, 4482-4502;
Angew. Chem. 2008, 120, 4558-4579.
M. Hirano, N. Komine, E. Arata, T. Gridneva, A. Hatori, N. Kaizawa, K. Kamakura, A. Kuramochi, S. Kurita, S. Machida, H. Okada, A. Sawasaki, T. Uchino, Tetrahedron Lett. 2019, 60, 150924.
M. M. Heravi, M. Dehghani, V. Zadsirjan, Tetrahedron: Asymmetry 2016, 27, 513-588.
T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844.
T. Yasukawa, H. Miyamura, S. Kobayashi, Acc. Chem. Res. 2020, 53, 2950-2963.
K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett. 2008, 10, 4387-4389.
C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628-1629.
T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508-11509.
S. Abele, R. Inauen, D. Spielvogel, C. Moessner, J. Org. Chem. 2012, 77, 4765-4773.
T. Nishimura, H. Kumamoto, M. Nagaosa, T. Hayashi, Chem. Commun. 2009, 5713-5715.
Y. Otomaru, N. Tokunaga, R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 307-310.
Y. Otomaru, A. Kina, R. Shintani, T. Hayashi, Tetrahedron: Asymmetry 2005, 16, 1673-1679.
A. Kina, K. Ueyama, T. Hayashi, Org. Lett. 2005, 7, 5889-5892.
F. Läng, F. Breher, D. Stein, H. Grützmacher, Organometallics 2005, 24, 2997-3007.
M.-C. Melcher, T. Ivšić, C. Olagnon, C. Tenten, A. Lützen, D. Strand, Chem. Eur. J. 2018, 24, 2344-2348.
M.-C. Melcher, B. Rolim Alves da Silva, T. Ivšić, D. Strand, ACS Omega 2018, 3, 3622-3630.
M. A. Esteruelas, L. A. Oro, Coord. Chem. Rev. 1999, 193-195, 557-618.
T. Nishimura, H. Makino, M. Nagaosa, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 12865-12867.
T. Nishimura, A. Noishiki, T. Hayashi, Chem. Commun. 2012, 48, 973-975.
R. Takechi, T. Nishimura, Chem. Commun. 2015, 51, 8528-8531.
Y. Pan, X. Lu, H. Qiu, T. Hayashi, Y. Huang, Org. Lett. 2020, 22, 8413-8418.
Y. Huang, T. Hayashi, J. Am. Chem. Soc. 2016, 138, 12340-12343.
Y. Huang, T. Hayashi, J. Am. Chem. Soc. 2015, 137, 7556-7559.
K. M.-H. Lim, T. Hayashi, J. Am. Chem. Soc. 2015, 137, 3201-3204.
M. Umeda, K. Sakamoto, T. Nagai, M. Nagamoto, Y. Ebe, T. Nishimura, Chem. Commun. 2019, 55, 11876-11879.
T. Nishimura, Y. Ichikawa, T. Hayashi, N. Onishi, M. Shiotsuki, T. Masuda, Organometallics 2009, 28, 4890-4893.
Separation by crystallization of menthol ethers was also used, but apparently has been abandoned: T. Nishimura, M. Nagaosa, T. Hayashi, Chem. Lett. 2008, 37, 860-861.
S. C. Cohen, M. L. N. Reddy, D. M. Roe, A. J. Tomlinson, A. G. Massey, J. Organomet. Chem. 1968, 14, 241-251.
D. S. Perekalin, A. V. Kolos, Mendeleev Commun. 2021, 31, 1-7.
Similar situation has been observed previously for rhodium complexes with diferent chiral ligands: M. Mayr, C. J. R. Bataille, S. Gosiewska, J. A. Raskatov, J. M. Brown, Tetrahedron: Asymmetry 2008, 19, 1328-1332.
L. Falivene, Z. Cao, A. Petta, L. Serra, A. Poater, R. Oliva, V. Scarano, L. Cavallo, Nat. Chem. 2019, 11, 872-879.
D. Franco, M. Gómez, F. Jiménez, G. Muller, M. Rocamora, M. A. Maestro, J. Mahía, Organometallics 2004, 23, 3197-3209.
L. Gong, M. Wenzel, E. Meggers, Acc. Chem. Res. 2013, 46, 2635-2644.
J. Ma, X. Zhang, X. Huang, S. Luo, E. Meggers, Nat. Protoc. 2018, 13, 605-632.
E. Meggers, Chem. Eur. J. 2010, 16, 752-758.
E. Meggers, Eur. J. Inorg. Chem. 2011, 2911-2926.
D. G. Gusev, Organometallics 2013, 32, 4239-4243.
Noteworthy, the chromatographic separation of the diastereomers 4 a and 5 a was not successful.
V. K. Aggarwal, G. Y. Fang, A. T. Schmidt, J. Am. Chem. Soc. 2005, 127, 1642-1643.
J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem. 2005, 1479-1492.
Y. Pang, Q. He, Z.-Q. Li, J.-M. Yang, J.-H. Yu, S.-F. Zhu, Q.-L. Zhou, J. Am. Chem. Soc. 2018, 140, 10663-10668.
D. Chen, X. Zhang, W.-Y. Qi, B. Xu, M.-H. Xu, J. Am. Chem. Soc. 2015, 137, 5268-5271.
N. Otog, S. Chanthamath, I. Fujisawa, S. Iwasa, Eur. J. Org. Chem. 2021, 1564-1567.
Q. Cheng, S. Zhu, Y. Zhang, X. Xie, Q. Zhou, J. Am. Chem. Soc. 2013, 135, 14094-14097.
S. Hyde, J. Veliks, B. Liégault, D. Grassi, M. Taillefer, V. Gouverneur, Angew. Chem. Int. Ed. 2016, 55, 3785-3789;
Angew. Chem. 2016, 128, 3849-3853.
S. B. J. Kan, X. Huang, Y. Gumulya, K. Chen, F. H. Arnold, Nature 2017, 552, 132-136.
K. Chen, X. Huang, S.-Q. Zhang, A. Z. Zhou, S. B. J. Kan, X. Hong, F. H. Arnold, Synlett 2019, 30, 378-382.
This type of borane adduct was chosen to achieve better separation of enantiomers of the products by analytical HPLC. Similar results were obtained with more common and commercially available BH3⋅NEt3.
B. Dutta, B. F. E. Curchod, P. Campomanes, E. Solari, R. Scopelliti, U. Rothlisberger, K. Severin, Chem. Eur. J. 2010, 16, 8400-8409.
For the closely related reaction see: D. Chen, D.-X. Zhu, M.-H. Xu, J. Am. Chem. Soc. 2016, 138, 1498-1501.
H. M. L. Davies, D. Morton, Chem. Soc. Rev. 2011, 40, 1857.
D. Gillingham, N. Fei, Chem. Soc. Rev. 2013, 42, 4918-4931.
H. Keipour, V. Carreras, T. Ollevier, Org. Biomol. Chem. 2017, 15, 5441-5456.
C. Werlé, R. Goddard, P. Philipps, C. Farès, A. Fürstner, J. Am. Chem. Soc. 2016, 138, 3797-3805.
X. Li, D. P. Curran, J. Am. Chem. Soc. 2013, 135, 12076-12081.
B. Xu, S. Zhu, X. Xie, J. Shen, Q. Zhou, Angew. Chem. Int. Ed. 2011, 50, 11483-11486;
Angew. Chem. 2011, 123, 11685-11688.
Y.-Y. Ren, S.-F. Zhu, Q.-L. Zhou, Org. Biomol. Chem. 2018, 16, 3087-3094.
The formation of the adducts R-I and S-I from [(S,S-iPr2-TFB)RhCl] and diazoester 8 a has favorable enthalpy but unfavorable entropy.
The difference between activation barriers of R-TS2 and S-TS2 also favors the formation of R-enantiomer of the product. However, we assume that it is less relevant because the formation of carbene intermediates R-II and S-II is irreversible and their ratio is fixed by the difference of R-TS1 and S-TS1.
Alternative attack of carbene by the hydrogen atom of benzamide has at least 47 kcal mol−1 activation barrier according to the potential energy scan.
Z. Zhou, Y. Tan, T. Yamahira, S. Ivlev, X. Xie, R. Riedel, M. Hemming, M. Kimura, E. Meggers, Chem 2020, 6, 2024-2034.
M. A. Bau, S. Wiesler, S. L. Younas, J. Streuff, Chem. Eur. J. 2019, 25, 10531-10545.
T. Punniyamurthy, M. Mayr, A. S. Dorofeev, C. J. R. Bataille, S. Gosiewska, B. Nguyen, A. R. Cowley, J. M. Brown, Chem. Commun. 2008, 5092-5094.