10.1002/anie.201802468
Angewandte Chemie International Edition
COMMUNICATION
Zhang, Y. Xiao, J. Zhang, Adv. Synth. Catal. 2013, 355, 2793-2797; d)
Z. Chen, Y. Xiao, J. Zhang, Eur. J. Org. Chem. 2013, 4748-4751; e) Z.
Chen, Z. Tian, J. Zhang, J. Ma, J. Zhang, Chem. Eur. J. 2012, 18,
8591-8595.
W. Zhou, H.-H. Wu, J. Zhang, Chem, Commun. 2017, 53, 5661-5664;
c) Y. Liao, X. Liu, Y. Zhang, Y. Xu, Y. Xia, L. Lin, X. Feng, Chem. Sci.
2016, 7, 3775-3779; d) L. Yang, A. Khan, R. Zheng, L. Y. Jin, Y. J.
Zhang, Org. Lett. 2015, 17, 6230-6233; e) S. K. Nimmagadda, Z. Zhang,
J. C. Antilla, Org. Lett. 2014, 16, 4098-4101; f) D. M. Rubush, T. Rovis,
Synlett 2014, 25, 713-717; g) Y. Fukata, K. Asano, S. Matsubara,
Chem. Lett. 2013, 42, 355-357; h) K. S. Williamson, T. P. Yoon, J. Am.
Chem. Soc. 2012, 134, 12370-12373; i) Z. Jin, X. Wang, H. Huang, X.
Liang, J. Ye, Org. Lett. 2011, 13, 564-567; j) D. J. Michaelis, K. S.
Williamson, T. P. Yoon, Tetrahedron 2009, 65, 5118-5124.
[4]
[5]
For a review, see: a) C. Martín, G. Fiorani, A. W. Kleij, ACS Catal. 2015,
5, 1353-1370. For selected recent examples, see: b) J. A. Castro-Osma,
A. Earlam, A. Lara-Sánchez, A. Otero, M. North, ChemCatChem 2016,
8, 2100-2108; c) P. Wang, J. Qin, D. Yuan, Y. Wang, Y. Yao,
ChemCatChem 2015, 7, 1145-1151; d) C. Beattie, M. North, Chem. Eur.
J. 2014, 20, 8182-8188, and references cited therein.
a) J.-J. Suo, J. Du, Q.-R. Liu, D. Chen, C.-H. Ding, Q. Peng, X.-L. Hou,
Org. Lett. 2017, 19, 6658-6661; b) Q. Cheng, H.-J. Zhang, W.-J. Yue,
S.-L. You, Chem 2017, 3, 428-436; c) C. Ma, Y. Huang, Y. Zhao, ACS
Catal. 2016, 6, 6408-6412; d) X. Yuan, L. Lin, W. Chen, W. Wu, X. Liu,
X. Feng, J. Org. Chem. 2016, 81, 1237-1243; e) W. Chen, Y. Xia, L. Lin,
X. Yuan, S. Guo, X. Liu, X. Feng, Chem. Eur. J. 2015, 21, 15104-
15107; f) W. Chen, X. Fu, L. Lin, X. Yuan, W. Luo, J. Feng, X. Liu, X.
Feng, Chem. Commun. 2014, 50, 11480-11483; g) W. Chen, L. Lin, Y.
Cai, Y. Xia, W. Cao, X. Liu, X. Feng, Chem. Commun. 2014, 50, 2161-
2163; h) Z. Liu, X. Feng, H. Du, Org. Lett. 2012, 14, 3154-3157; i) W.-Q.
Wu, C.-H. Ding, X.-L. Hou, Synlett 2012, 23, 1035-1038; j) M. B.
Shaghafi, R. E. Grote, E. R. Jarvo, Org. Lett. 2011, 13, 5188-5191; k) C.
Larksarp, H. Alper, J. Org. Chem. 1998, 63, 6229-6233; l) C. Larksarp,
H. Alper, J. Am. Chem. Soc. 1997, 119, 3709-3715.
[12] a) T. Takeda, M. Terada, J. Am. Chem. Soc. 2013, 135, 15306-15309;
b) T. Takeda, M. Terada, Aust. J. Chem. 2014, 67, 1124-1128; c) A.
Kondoh, M. Oishi, T. Takeda, M. Terada, Angew. Chem. 2015, 127,
16062-16065; Angew. Chem. Int. Ed. 2015, 54, 15836-15839; d) T.
Takeda, A. Kondoh, M. Terada, Angew. Chem. 2016, 128, 4812-4815;
Angew. Chem. Int. Ed. 2016, 55, 4734-4737.
[13] Superbases for Organic Synthesis (Ed.: T. Ishikawa), John Wiley &
Sons, Chippenham, 2009.
[14] (Z) configuration of major isomer of 5aa was unambiguously
determined by X-ray crystallographic analysis. CCDC No.1822256. See
the Supporting Information for details.
+
[15] The pKBH of achiral bis(guanidino)iminophosphorane 12 possessing a
backbone similar to 1 was reported to be 26.8 in THF, see: A. A.
Kolomeitsev, I. A. Koppel, T. Rodima, J. Barten, E. Lork, G.-V.
Röschenthaler, I. Kaljurand, A. Kütt, I. Koppel, V. Mӓemets, I. Leito, J.
Am. Chem. Soc. 2005, 127, 17656-17666.
[6]
[7]
A. Kondoh, K. Odaira, M. Terada, Angew. Chem. 2015, 127, 11392-
11396; Angew. Chem. Int. Ed. 2015, 54, 11240-11244.
a) D. Zhou, X. Yu, J. Zhang, W. Wang, H. Xie, Org. Biomol. Chem.
2016, 14, 6193-6196; b) J. Liu, F.-M. Zhu, Y.-B. Chu, L.-H. Huang, Y.-F.
Zhou, Tetrahedron: Asymmetry 2015, 26, 1130-1137; c) T.-Z. Li, X.-B.
Wang, F. Sha, X.-Y. Wu, Tetrahedron 2013, 69, 7314-7319.
[8]
[9]
For a review, see: C. Agami, F. Couty, Eur. J. Org. Chem. 2004, 677-
685.
[16] CCDC No.1822255 for racemic 4aa and CCDC No.1822257 for (R)-7.
See the Supporting Information for details.
a) H. Nakano, Y. Okuyama, E. Kwon, Heterocycles 2014, 89, 1-26; b) C.
Wolf, H. Xu, Chem. Commun. 2011, 47, 3339-3350; c) T. Arai, Y. Ogino,
T. Sato, Chem. Commun. 2013, 49, 7776-7778.
[17] See the Supporting Information for details.
[18] The reaction of ,-epoxysulfone having an ethoxycarbonyl group at the
R1 position was also examined under the optimized reaction conditions.
However, the conversion of the substrate was very low (ca. 30%), and
the corresponding oxazolidine was not obtained. The introduction of
such electron-withdrawing groups seems to have a detrimental effect
on the reaction system.
[10] For selected examples, see: a) J. D. Scott, R. M. Williams, Chem. Rev.
2002, 102, 1669-1730; b) L. Yu, W. Zhou, Z. Wang, Bio. Med. Chem.
Lett. 2011, 21, 1541-1544; c) K. Ii, S. Ichikawa, B. Al-Dabbagh, A.
Bouhss, A. Matsuda, J. Med. Chem. 2010, 53, 3793-3813; d) J. D.
Scott, R. M. Williams, J. Am. Chem. Soc. 2002, 124, 2951-2956; e) G.
P. Moloney, D. J. Craik, M. N. Iskander, T. L. Nero, J. Chem. Soc.,
Perkin Trans. 2. 1998, 199-206.
[19] The reaction of (E)-6a with 3a under the optimized reaction conditions
resulted in the formation of (E)-5aa in 95% yield with <1%ee.
[20] E. O. Volz, G. W. O’Neil, J. Org. Chem. 2011, 76, 8428-8432.
[11] For selected recent examples on catalytic enantioselective synthesis of
1,3-oxazolidines, see: a) S. Tanaka, R. Gunasekar, T. Tanaka, Y. Iyoda,
Y. Suzuki, M. Kitamura, J. Org. Chem. 2017, 82, 9160-9170; b) X. Wu,
This article is protected by copyright. All rights reserved.