Please do not adjust margins
ChemComm
DOI: 10.1039/C7CC01391D
COMMUNICATION
Journal Name
The rhodium first go though ligand exchange with
4
5
J. Schutter, J. Park, C. Leung, P. Gormley, Y. Lin, Z. Hu, A.
Berghuis, J. Poirier and Y. Tsantrizos, J. Med. Chem., 2014,
57, 5764.
diphenylphosphine oxide to form complex A, then the double
bond of allylamine was coordinated to the metal complex A,
followed by C-H addition of allylic carbon to generate the Rh-allyl
intermediates B. Then, C-H reductive elimination led the
a) P. Tongcharoensirikul, A. I. Suarez, T. Voelker, C. M.
Thompson, J. Org. Chem., 2004, 69, 2322. b) H. Xie, A. Song,
X. Zhang, X. Chen, H. Li, C. Sheng, W. Wang, Chem. Commun.,
2013, 49, 928.
formation of enamine intermediates
diphenylphosphine oxide experiences a nucleophilic addition
to enamine intermediates to produce the
C. At the same time, the
C
6
a) R. A. Cherkasov, V. I. Galkin, Russ. Chem. Rev. 1998, 67
857; b) D. Seidel, Acc. Chem. Res., 2015, 48, 317.
,
hydrophosphonylated product 3aa and release the Rh-catalyst
to finish the catalytic cycle. Same mechanism is proposed for
Ni(II)-catalyzed transformation process.
7
8
9
J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713.
H. Takuya, M. Keiji, Chem. Rev. 2007, 107, 5656.
a) O. Baslé and C. Li, Chem. Commun. 2009, 4124; b) S. A.
Girard, T. Knauber, C.-J. Li. Angew. Chem. Int. Ed. 2014, 53
4. c) M.-X. Cheng, R.-S. Ma, Q. Yang and S.-D. Yang, Org.
Lett., 2016, 18, 3262.
0 a J. Royer, M. Bonin and L. Micouin, Chem, Rev. 2004, 104
311; b) B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi
,
7
1
)
2
and C. A. Maryanoff, Chem. Rev. 2004, 104, 1431; (c) W. N.
Speckamp and M. J. Moolenaar, Tetrahedron, 2000, 3817; (d
S. T. Le Quement, R. Petersen, M. Meldal and T. E. Nielsen,
Biopolymers, 2010, 94, 242; e) E. Ascic, C. L. Hansen, S. T. Le
Quement and T. E. Nielsen, Chem. Commun., 2012, 48, 3345;
f) Q. Cai, X.-W. Liang, S.-G. Wang, J.-W. Zhang, X. Zhang and
S.-L. You, Org. Lett., 2012, 14, 5022; g) E. Ascic, J. F. Jensen
and T. E. Nielsen, Angew. Chem. Int. Ed. 2011, 50, 5188; h)
Y.-C. Shi, S.-G. Wang, Q. Yin and S.-L. You, Org. Chem. Front.,
)
Scheme 4. Possible Mechanism of Cascade Sequence
Transformations of Allylamine
2
014, 1, 39; i) K. Tani, Z. Yamagata, S. Akutagawa, H.
Conclusions
Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori
In summary, we have developed a novel and efficient
method for the construction of α-aminophosphonates by a
cascade sequence of allylamine isomerization and
hydrophosphonylation. The reaction process benefits from a
broad selection of the comparatively stable and readily
available substrates, and potential biological useful products
are produced in moderate to excellent yields.
and S. Otsuka, J . Am. Chem. Soc., 1984, 106, 5208.
1
1
1 K. Sorimachi and M. Terada, J. Am. Chem. Soc., 2008, 130
4452.
,
1
2 a) C. L. Hansen, J. W. Clausen, R. G. Ohm, E. Ascic, S. T. Le
Quement, D. Tanner and T. E. Nielsen, J. Org. Chem., 2013,
78, 12545; b) E. Ascic, R. G. Ohm, R. Petersen, M. R. Hansen,
C. L. Hansen, D. Madsen, D. Tanner and T. E. Nielsen, Chem.
Eur. J., 2014, 20, 3297.
1
3 a) P. Merino, E. Marqués-López and R. P. Herrera, Adv. Synth.
Acknowledgement
Catal. 2008, 350, 1195; b) V. Rodriguez-Ruiz, R. Carlino, S.
Bezzenine-Lafollée, R. Gil, D. Prim, E. Schulza and J.
Hannedouche, Dalton Trans., 2015, 44, 12029; c) Y. Gao, H.
Deng, S. Zhang, W. Xue, Y. Wu, H. Qiao, P. Xu and Y. Zhao, J.
Org. Chem., 2015, 80, 1192.
We are grateful for the NSFC (Nos. 21472076 and 21532001) and
Program for Changjiang Scholars and Innovative Research Team in
University (IRT_15R28 and lzujbky-2016-sp05) financial support.
1
4 a) M. Vilches-Herrera, L. Domke and A. Börner, ACS Catal.
Notes and references
2
014, 4, 1706; b) B. Soumik, Comments on Inorganic
1
a) E. D. Naydenova, P. T. Todorov and K. D. Troev, Amino
Acids, 2010, 38, 23; b) M. C. Allen, W. Fuhrer, B. Tuch, R.
Wade and J. M. Wood, J. Med. Chem. 1989, 32, 1652; c) Ł.;
Winiarski, J. Oleksyszyn and M. Sieṅczyk, J. Med. Chem. 2012,
Chemistry, 2015, 35, 300.
1
1
5 a) J. Vicario, P. Ortiz and F. Palacios, Eur. J. Org. Chem., 2013,
7
095.
6 a) L. Wang, C. Liu, R. Bai, Y. Pana and A. Lei, Chem. Commun.,
013, 49, 7923; b) G. Erdogan and D. B. Grotjahn, J. Am.
Chem. Soc. 2009, 131, 10354; c D. B. Grotjahn, C. R. Larsen,
J. L. Gustafson, R. Nair and A. Sharma, J. Am. Chem. Soc.
007, 129, 9592; d) J. Tao, F. Sun and T. J. Fang, Organomet.
5
5
, 6541. d) D. A. McLeod, R. I. Brinkworth, J. A. Ashley, K. D.
Janda and P. Wirsching, Bioorg. Med. Chem. Lett. 1991,
53.
2
1,
)
6
2
3
B. Lejczak, P. Kafarski, H. Sztajer and P. Mastalerz, J. Med.
Chem., 1986, 29, 2212.
2
Chem. 2012, 698, 1; e) E. Richmond, I. U. Khan and J. Moran,
Chem. Eur. J. 2016, 22, 12274.
J. Fuhrmann, V. Subramanian and P. R. Thompson, Angew.
Chem. Int. Ed., 2015, 54, 14715.
4
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins