10.1002/chem.201700110
Chemistry - A European Journal
FULL PAPER
[20]
[21]
K. Soai, T. Kawasaki, A. Matsumoto, Chem. Rec. 2014, 14, 70–83.
H. Mineki, Y. Kaimori, T. Kawasaki, A. Matsumoto, K. Soai,
Tetrahedron Asymmetry 2013, 24, 1365–1367.
M. Sakamoto, A. Unosawa, S. Kobaru, A. Saito, T. Mino, T. Fujita,
Angew. Chem. 2005, 117, 5659-5662; Angew. Chem. Int. Ed. 2005,
44, 5523–5526.
synthesized enantioenriched or enantiopure amino acids
derivatives and found condition for their deprotection without
racemization. We were also able to get enantioenriched amino
alcohol. Moreover, we were able to choose the initial small
crystal to get either the R or the S enantiomer of the final amino
acid. Thanks to VCD analyses, we have also determined the
absolute configuration of the crystal of the starting oxazolidinone
and then rationalized the observed stereoselectivity. Other
electrophiles are under investigation in our group in order to
enlarge the spectrum of the method.
[22]
[23]
[24]
[25]
[26]
[27]
[28]
[29]
[30]
[31]
M. Sakamoto, M. Kato, Y. Aida, K. Fujita, T. Mino, T. Fujita, J. Am.
Chem. Soc. 2008, 130, 1132–1133.
M. Sakamoto, F. Yagishita, A. Saito, S. Kobaru, A. Unosawa, T. Mino,
T. Fujita, Photochem. Photobiol. Sci. 2011, 10, 1387–1389.
F. Yagishita, N. Takagishi, H. Ishikawa, Y. Kasashima, T. Mino, M.
Sakamoto, Eur. J. Org. Chem. 2014, 2014, 6366–6370.
M. Sakamoto, T. Iwamoto, N. Nono, M. Ando, W. Arai, T. Mino, T.
Fujita, J. Org. Chem. 2003, 68, 942–946.
M. Sakamoto, A. Unosawa, S. Kobaru, K. Fujita, T. Mino, T. Fujita,
Chem. Commun. 2007, 3586–3588.
M. Sakamoto, K. Fujita, F. Yagishita, A. Unosawa, T. Mino, T. Fujita,
Chem. Commun. 2011, 47, 4267–4269.
F. Yagishita, T. Mino, T. Fujita, M. Sakamoto, Org. Lett. 2012, 14,
2638–2641.
F. Bouillère, R. Guillot, C. Kouklovsky, V. Alezra, Org Biomol Chem
2011, 9, 394–399.
C. T. Hoang, F. Bouillère, S. Johannesen, A. Zulauf, C. Panel, A.
Pouilhès, D. Gori, V. Alezra, C. Kouklovsky, J. Org. Chem. 2009, 74,
4177–4187.
C. T. Hoang, V. Alezra, R. Guillot, C. Kouklovsky, Org. Lett. 2007, 9,
2521–2524.
A. Stanovych, R. Guillot, C. Kouklovsky, E. Miclet, V. Alezra, Amino
Acids 2014, 46, 2753–2757.
N. Auberger, A. Stanovych, S. Thétiot-Laurent, R. Guillot, C.
Kouklovsky, S. C. des Combes, C. Pacaud, I. Devillers, V. Alezra,
Amino Acids 2016, 48, 2237–2242.
Acknowledgements
We thank the Marie Curie program for a IIF fellowship (post-
doctoral fellowship to B.V., grant PIIF-GA-2011-300491) and the
ANR (Agence Nationale de la Recherche; ANR grant n°ANR-08-
JCJC0099, doctoral grant to T.T.M.) for financial support. The
authors thank Dr. David Berardan (ICMMO) for assistance and
loan of planetary ball mill. This work was supported by the
computing facilities of the CRCMM, ‘Centre Régional de
Compétences en Modélisation Moléculaire de Marseille’.
[32]
[33]
[34]
[35]
[36]
V. Alezra, T. Kawabata, Synthesis 2016, 48, 2997–3016.
M. Branca, S. Pena, R. Guillot, D. Gori, V. Alezra, C. Kouklovsky, J.
Am. Chem. Soc. 2009, 131, 10711–10718.
M. Branca, D. Gori, R. Guillot, V. Alezra, C. Kouklovsky, J. Am. Chem.
Soc. 2008, 130, 5864–5865.
T. T. Mai, B. Viswambharan, D. Gori, C. Kouklovsky, V. Alezra, J. Org.
Chem. 2012, 77, 8797–8801.
B. Viswambharan, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra, Org.
Lett. 2014, 16, 788–791.
T. T. Mai, M. Branca, D. Gori, R. Guillot, C. Kouklovsky, V. Alezra,
Angew. Chem. 2012, 124, 5065-5068; Angew. Chem. Int. Ed. 2012,
51, 4981–4984.
A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink,
N. Westlund, S. A. Yasin, Tetrahedron 1998, 54, 13277–13294.
M. S. Betson, J. Clayden, M. Helliwell, P. Johnson, L. W. Lai, J. H.
Pink, C. C. Stimson, N. Vassiliou, N. Westlund, S. A. Yasin, et al., Org.
Biomol. Chem. 2006, 4, 424.
R. A. Bragg, J. Clayden, G. A. Morris, J. H. Pink, Chem. – Eur. J. 2002,
8, 1279–1289.
K. Burger, H. Sehedel, J. Spengler, Amino Acids 1999, 16, 287–295.
P. S. Hynes, D. Stranges, P. A. Stupple, A. Guarna, D. J. Dixon, Org.
Lett. 2007, 9, 2107–2110.
The yields of all these syntheses were not optimized, the aim was just
to get enough product for crystallization and determine if the
compound crystallize in a chiral space group or not.
We have previously noted that, apart from the formaldehyde
derivatives, the oxazolidinones synthesized starting from an -amino
acid and a ketone possess all this cis conformation: the aromatic
moiety, more hindered is on the tertiary carbon side, whereas the
oxygen is on the quaternary carbon side.
Keywords: Amino acid • Asymmetric synthesis • VCD • Crystal •
Frozen chirality
[37]
[38]
[39]
[40]
[1]
B. L. Feringa, R. A. van Delden, Angew. Chem. 1999, 111, 3624-
3645; Angew. Chem. Int. Ed. 1999, 38, 3418–3438.
I. Weissbuch, M. Lahav, Chem. Rev. 2011, 111, 3236–3267.
P. de Marcellus, C. Meinert, M. Nuevo, J.-J. Filippi, G. Danger, D.
Deboffle, L. Nahon, L. Le Sergeant d’Hendecourt, U. J. Meierhenrich,
Astrophys. J. 2011, 727, L27.
[2]
[3]
[4]
[5]
N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996,
273, 1686–1688.
[41]
[42]
W. L. Noorduin, A. A. C. Bode, M. van der Meijden, H. Meekes, A. F.
van Etteger, W. J. P. van Enckevort, P. C. M. Christianen, B. Kaptein,
R. M. Kellogg, T. Rasing, et al., Nat. Chem. 2009, 1, 729–732.
I. Myrgorodska, C. Meinert, Z. Martins, L. Le Sergeant d’Hendecourt,
U. J. Meierhenrich, Angew. Chem. 2015, 127, 1420-1430; Angew.
Chem. Int. Ed. 2015, 54, 1402–1412.
[6]
[43]
[44]
[45]
[7]
N. Micali, H. Engelkamp, P. G. van Rhee, P. C. M. Christianen, L. M.
Scolaro, J. C. Maan, Nat. Chem. 2012, 4, 201–207.
W. L. Noorduin, E. Vlieg, R. M. Kellogg, B. Kaptein, Angew. Chem.
2009, 121, 9778-9784; Angew. Chem. Int. Ed. 2009, 48, 9600–9606.
T. Matsuura, H. Koshima, J. Photochem. Photobiol. C Photochem.
Rev. 2005, 6, 7–24.
[8]
[46]
[47]
[9]
[10]
[11]
[12]
[13]
[14]
[15]
M. Sakamoto, T. Mino, in Adv. Cryst. Process. (Ed.: Y. Mastai),
InTech, 2012.
J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates, and
Resolutions, Wiley, 1981.
A. Lennartson, S. Olsson, J. Sundberg, M. Håkansson, Angew. Chem.
2009, 121, 3183-3186; Angew. Chem. Int. Ed. 2009, 48, 3137–3140.
S. Olsson, P. M. Björemark, T. Kokoli, J. Sundberg, A. Lennartson, C.
J. McKenzie, M. Håkansson, Chem. – Eur. J. 2015, 21, 5211–5219.
S. Olsson, A. Lennartson, M. Håkansson, Chem. – Eur. J. 2013, 19,
12415–12423.
O. Tissot, M. Gouygou, F. Dallemer, J.-C. Daran, G. G. A. Balavoine,
Angew. Chem. 2001, 113, 1110-1112; Angew. Chem. Int. Ed. 2001,
40, 1076–1078.
[48]
We chose the methyl signals because of the absence of multiplicity
and applied the following equation: G≠ = -RTc*[22.96 + ln(Tc/)] in
which R is the gas constant, TC the coalescence temperature and
is the frequency differ-ence between the chemical shifts of the two
separated methyl groups at low temperature, see: R. J. Abraham, P.
Loftus, Proton and Carbon-13 NMR Spectroscopy: An Integrated
Approach, John Wiley&Sons, New York, 1985.
D. M. Bender, R. M. Williams, J. Org. Chem. 1997, 62, 6690–6691.
L. Lecointe, V. Rolland, L. Pappalardo, M. l. Roumestant, P. h.
Viallefont, J. Martine, J. Pept. Res. 2000, 55, 300–307.
See supporting information for details
D. J. A. Schedler, J. Li, B. Ganem, J. Org. Chem. 1996, 61, 4115–
4119.
J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem.
Soc. 2007, 129, 3408–3419.
D. A. Evans, T. C. Britton, J. A. Ellman, Tetrahedron Lett. 1987, 28,
6141–6144.
[49]
[50]
[16]
[17]
[18]
M. Sakamoto, J. Photochem. Photobiol. C Photochem. Rev. 2006, 7,
183–196.
[51]
[52]
F. Yagishita, M. Sakamoto, T. Mino, T. Fujita, Org. Lett. 2011, 13,
6168–6171.
T. Kawasaki, T. Sasagawa, K. Shiozawa, M. Uchida, K. Suzuki, K.
Soai, Org. Lett. 2011, 13, 2361–2363. In that case, chiral crystals of
racemic DL-diserinium sulfate, space group P212121, was used as a
chiral initiator.
[53]
[54]
[19]
I. Sato, K. Kadowaki, K. Soai, Angew. Chem. 2000, 112, 1570-1572;
Angew. Chem. Int. Ed. 2000, 39, 1510–1512.
This article is protected by copyright. All rights reserved.