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Organic & Biomolecular Chemistry
Page 10 of 10
DOI: 10.1039/C5OB02352A
ARTICLE
Journal Name
Q. Tu, Org. Lett., 2004, 6, 169−172; (e) Z. Zhou, Y. Sun and A.
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(a) B. Mohar, A. Valleix, J.-R. Desmurs, M. Felemez, A. Wagner
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D. Šterk, M. Stephan and B. Mohar, Tetrahedron: Asymmetry,
2002, 13, 2605−2608; (c) Z. Luo, F. Qin, S. Yan and X. Li, 14 For a kinetic resolution of racemic cis-3-hydroxymethyl-indanol
Tetrahedron: Asymmetry, 2012, 23, 333−338; (d) W.-W. Wang,
Z.-M. Li, L. Su, Q.-R. Wang and Y.-L. Wu, J. Mol. Cat. A: Chem.,
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Zhang, J. Chen and Z. Hou, Catal. Commun., 2015, 67, 90−94.
For 2nd generation Ru(II) complexes, see: (a) J. Hannedouche, G.
J. Clarkson and M. Wills, J. Am. Chem. Soc., 2004, 126, 986−987;
(b) A. Kišić, M. Stephan and B. Mohar, Org. Lett., 2013, 15,
1614−1617; (c) A. Kišić, M. Stephan and B. Mohar, Adv. Synth.
Catal., 2014, 356, 3193−3198.
or -tetralol by oxidation in acetone using [Ru(TsDPEN)(p-
cymene)], see: M. Caro, M. Torrado, C. F. Masaguer and E.
Raviña, Tetrahedron: Asymmetry, 2003, 14, 3689−3696.
15 A preparation of enantiomeric 3-ethoxycarbonyl-1-indanone
(96% ee) by asymmetric hydroacylation of o-formyl-atropic acid
ethyl ester using {Rh[(R)-BINAP]}ClO4 has been achieved. For
this, see: K. Kundu, J. V. McCullagh and A. T. Morehead, Jr., J.
Am. Chem. Soc., 2005, 127, 16042−16043.
16 (a) P. A. Dub and T. Ikariya, J. Am. Chem. Soc., 2013, 135,
2604−2619; (b) A. Matsuoka, C. A. Sandoval, M. Uchiyama, R.
Noyori and H. Naka, Chem. Asian J., 2015, 10, 112−115.
4
5
For 3rd generation Ru(II) complexes, see: (a) A. M. Hayes, D. J.
Morris, G. J. Clarkson and M. Wills, J. Am. Chem. Soc., 2005,
127, 7318−7319; (b) T. Touge, T. Hakamata, H. Nara, T. 17 H. O. House and C. B. Hudson, J. Org. Chem., 1970, 35, 647−651.
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Chem. Soc., 2011, 133, 14960−14963; (c) R. Soni, K. E. Jolley, G.
J. Clarkson and M. Wills, Org. Lett., 2013, 15, 5110−5113; (d) R. 19 C. J. O’Donnell, R. A. Singer, J. D. Brubaker and J. D. McKinley, J.
Soni, T. H. Hall, B. P. Mitchell, M. R. Owen and M. Wills, J. Org. Org. Chem., 2004, 69, 5756−5759.
Chem., 2015, 80, 6784−6793; (e) A. Kišić, M. Stephan and B. 20 H. Malik, F. P. J. T. Rutjes and B. Zwanenburg, Tetrahedron,
Mohar, Adv. Synth. Catal., 2015, 357, 2540−2546. 2010, 66, 7198−7203.
(a) A. Hayes, G. Clarkson and M. Wills, Tetrahedron: Asymmetry, 21 Separation of rac syn-6 enantiomers by preparative HPLC was
2004, 15, 2079−2084; (b) B. Zhang, H. Wang, G.-Q. Lin and M.-H. outsourced to Chiral Technologies Europe (France).
Xu, Eur. J. Org. Chem., 2011, 4205−4211; (c) M. J. Palmer, J. A. 22 Separation of rac anti-6 enantiomers by preparative SFC was
Kenny, T. Walsgrove, A. M. Kawamoto and M. Wills, J. Chem. outsourced to WuXi AppTec Co., Ltd (China).
6488−6491.
6
7
Soc., Perkin Trans. 1, 2002, 416−427; (d) P. Roszkowski, J. K. 23 For chiral GC analysis, see: (a) ref. 5e. (b) ref. 3b.
Maurin and Z. Czarnocki, Tetrahedron: Asymmetry, 2013, 24,
643−650.
The preparation of (R)-3-hydroxymethyl-1,1-dioxo-benzo-1,2- anti-(3R,1'R)-
thiazolidine was described following related synthetic 1436154 [for S7-reduced] contain the supplementary
‡ CCDC-1436151 [for syn-(3S,1'R)-
6
·(S)-CSA], CCDC-1436152 [for
6
·(S)-CSA], CCDC-1436153 [for trans-
5
], and CCDC-
a
strategy. Therein, in addition to a 5-exo-type cyclization, the crystallographic data for this paper. These data can be obtained
formation of trans-(3R,4S)-4-hydroxy-3-hydroxymethyl-1,1- free of charge from The Cambridge Crystallographic Data Centre
dioxo-benzo-1,2-thiazinane
derived
from
cyclization occurred as well. For this, see: K. H. Ahn, H. H. Baek,
S. J. Lee and C.-W. Cho, J. Org. Chem., 2000, 65, 7690−7696.
J.-L. Liang, S.-X. Yuan, P. W. H. Chan and C.-M. Che, Org. Lett.,
2002, 4, 4507−4510.
8
9
C24H30N2O6S2, FW 506.62, monoclinic, space group P 21 (No. 4), a
= 12.5236(3), b = 7.53800(17), c = 12.9539(3) Å,
β = 92.676(2)°,
V = 1221.55(5) Å3, Z = 2, T = 150(2) K, dcalcd = 1.377 g cm–3, μ =
0.261 mm–1, 11729 measured reflections, 5599 unique
reflections (Rint = 0.0280), 324 refined parameters, R1 [I > 2σ(I)]
= 0.0482, wR2 [all data] = 0.1230.
10 P. A. Byrne and D. G. Gilheany, J. Am. Chem. Soc., 2012, 134,
9225–9239.
11 C24H30N2O6S2, FW 506.62, monoclinic, space group P 21 (No. 4), a
= 13.1356(2), b = 7.03520(10), c = 14.6189(2) Å,
β =
112.8645(8)°, V = 1244.81(3) Å3, Z = 2, T = 293(2) K, dcalcd = 1.352
g cm–3, μ = 0.256 mm–1, 20767 measured reflections, 5599
unique reflections (Rint = 0.0280), 323 refined parameters, R1 [I
> 2σ(I)] = 0.0474, wR2 [all data] = 0.1300.
12 For DKR during Ru-TsDPEN-catalyzed (S/C = 200) ATH of 2-
ethoxycarbonyl-1-indanone (S6 analog) (6 days, 81% yield,
cis/trans >99:1, 99% ee for cis) and 2-ethoxycarbonyl-1-
tetralone (S8 analog) (6 days, 90% yield, cis/trans >99:1, 99% ee
for cis) using HCO2H/Et3N 5:2 at rt, see: A. Ros, A. Magriz, H.
Dietrich, J. M. Lassaletta and R. Fernández, Tetrahedron, 2007,
63, 7532−7537.
13 For a review on DKR in ATH, see: (a) H. Pellisier, Tetrahedron,
2011, 67, 3769−3802. For selected recent DKR examples in ATH,
see: (b) B. Seashore-Ludlow, F. Saint-Dizier and P. Somfai, Org.
Lett., 2012, 14, 6334−6337; (c) K. M. Steward, E. C. Gentry and J.
S. Johnson, J. Am. Chem. Soc., 2012, 134, 7329−7332; (d) S.-M.
Son and H.-K. Lee, J. Org. Chem., 2014, 79, 2666−2681; (e) F. Xu,
M. J. Zacuto, Y. Kohmura, J. Rosen, A. Gibb, M. Alam, J. Scott
10 | Org. Biomol. Chem., 2015, 00, 1-3
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