Organic Letters
Letter
Notes
Mohar, B. Angew. Chem., Int. Ed. 2016, 55, 5294−5298. (d) Cheng, T.;
Ye, Q.; Zhao, Q.; Liu, G. Org. Lett. 2015, 17, 4972−4975. (e) Son, S.-
M.; Lee, H.-K. J. Org. Chem. 2014, 79, 2666−2681. (f) Xu, F.; Zacuto,
M. J.; Kohmura, Y.; Rosen, J.; Gibb, A.; Alam, M.; Scott, J.; Tschaen,
D. Org. Lett. 2014, 16, 5422−5425.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
The authors acknowledge the financial support from the
Slovenian Research Agency (research core funding No. P1-
■
(13) By analogy, DKR−ATH of 2-phenyl-1-tetralone employing
[Ru(S,S)-TsDPEN(p-cym)] (S/C = 50) in HCO H/Et N 5:2 at rt for
2
3
2
42). We thank Barbara Modec from the University of
77 h afforded cis-(1S,2R)-2-phenyl-1-tetralol in >97% de and 98% ee
(87% isolated yield). For this, see: Peach, P.; Cross, D. J.; Kenny, J. A.;
Ljubljana, for X-ray crystal structures determination.
Mann, I.; Houson, I.; Campbell, L.; Walsgrove, T.; Wills, M.
Tetrahedron 2006, 62, 1864−1876.
REFERENCES
■
(
14) For a paralleled Ru(II)-catalyzed ATH of 1,2-diketones, see:
(
6
1) (a) Ahn, K. H.; Kim, S.; Ham, C. Tetrahedron Lett. 1998, 39,
(
a) Murata, K.; Okano, K.; Miyagi, M.; Iwane, H.; Noyori, R.; Ikariya,
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̌
́
(
15) The absolute configurations of A6−A9 were attributed on the
(
2) (a) Takeuchi, Y.; Suzuki, T.; Satoh, A.; Shiragami, T.; Shibata, N.
basis of the stereoselectivity trend obtained for the (S,S)-DPEN-based
Ru(II)-catalyzed ATH of S1/S1′ and the structurally closely related 2-
J. Org. Chem. 1999, 64, 5708−5711. (b) Ahn, K. H.; Baek, H.-H.; Lee,
S. J.; Cho, C.-W. J. Org. Chem. 2000, 65, 7690−7696. (c) Sun, H. M.;
Liu, Z. P.; Tang, L. Q. Chin. Chem. Lett. 2008, 19, 907−910. (d) Ali, I.;
Al-Othman, Z. A.; Al-Warthan, A.; Alam, S. D.; Farooqi, J. A. Chirality
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Org. Biomol. Chem. 2016, 14, 2112−2120.
3) Conrow, R. E.; Dean, W. D.; Zinke, P. W.; Deason, M. E.;
10c
10c
13
12a
R-1-tetralones wherein R = H, Me, Ph, azolyls, or CH(OH)
12c
CF3.
For R = CO Me, see: Ros, A.; Magriz, A.; Dietrich, H.;
2
Lassaletta, J. M.; Fernan
́
dez, R. Tetrahedron 2007, 63, 7532−7537. For
2
R = SO Ph, see: Ding, Z.; Yang, T.; Shen, Z.; Zhang, Y. Chem.
2
Commun. 2009, 571−573.
(
(16) Racemic trans-aziridine was similarly used to prepare racemic
Sproull, S. J.; Dantanarayana, A. P.; DuPriest, M. T. Org. Process Res.
Dev. 1999, 3, 114−120.
syn-ULTAM by consecutive ring opening with NaN3 and hydro-
genation. However, this was carried out from a racemic trans-A1
(
4) Fernan
C. Chem. Commun. 2014, 50, 6046−6048.
5) Dydio, P.; Key, H. M.; Hayashi, H.; Clark, D. S.; Hartwig, J. F. J.
Am. Chem. Soc. 2017, 139, 1750−1753.
6) For Ru(II)-catalyzed AH or ATH of 3-R-1,1-dioxo-1,2-
́
dez-Salas, J. A.; Rodriguez-Fernan
́
dez, M. M.; Maestro, M.
2e
precursor (Scheme 1).
(
(
benzothiazoles, see: (a) Oppolzer, W.; Wills, M.; Starkemann, C.;
Bernardinelli, G. Tetrahedron Lett. 1990, 31, 4117−4120. (b) Ahn, K.
H.; Ham, C.; Kim, S.-K.; Cho, C.-W. J. Org. Chem. 1997, 62, 7047−
7
048. (c) Itsuno, S.; Takahashi, S. ChemCatChem 2017, 9, 385−388.
For Pd(II)-catalyzed AH of 3-R-1,1-dioxo-2H-1,2-benzothiazines, see:
d) Yu, C.-B.; Gao, K.; Wang, D.-S.; Shi, L.; Zhou, Y.-G. Chem.
Commun. 2011, 47, 5052−5054.
7) TsDPEN = (R,R)- or (S,S)-N-p-tosyl-1,2-diphenylethylene-
(
(
diamine; for its early application in ATH, see: (a) Fujii, A.;
Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem.
Soc. 1996, 118, 2521−2522. (b) Yamakawa, M.; Yamada, I.; Noyori, R.
Angew. Chem., Int. Ed. 2001, 40, 2818−2821.
1
(
8) The structure of S1 was assigned based on the H NMR of the
S1/S1′ mixture and the ATH result affording cis-A1 in 100% yield.
1
(
9) H NMR of S8 showed a single geometric isomer which most
likely corresponds to the indicated (Z)-configuration. For structural
analysis of the closely related (Z)-2-benzylidene-1-tetralone, see:
Kaluski, Z.; Skrzypczak-Jankun, E.; Orlov, V. D.; Borovoi, I. A. Bull.
Acad. Pol. Sci., Ser. Sci. Chim. 1978, 26, 869−876.
(
10) For recent reviews and articles on ATH, see: (a) Nedden, H. G.;
Zanotti-Gerosa, A.; Wills, M. Chem. Rec. 2016, 16, 2623−2643.
b) Foubelo, F.; Najera, C.; Yus, M. Tetrahedron: Asymmetry 2015, 26,
69−790. For ansa-Ru(II) cat. I and II, see: (c) Kisic, A.; Stephan,
(
7
́
̌
́
M.; Mohar, B. Adv. Synth. Catal. 2015, 357, 2540−2546 and current
Supporting Information. For cat. III, see: (d) Hayes, A. M.; Morris,
D. J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2005, 127, 7318−
7
́
319. (e) Cheung, F. K.; Lin, C.; Minissi, F.; Lorente Criville, A.;
Graham, M. A.; Fox, D. J.; Wills, M. Org. Lett. 2007, 9, 4659−4662.
For cat. IV, see: (f) Touge, T.; Hakamata, H.; Kobayashi, N.; Sayo, N.;
Saito, T.; Kayaki, Y.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 14960−
1
2
(
4963. (g) Parekh, V.; Ramsden, J. A.; Wills, M. Catal. Sci. Technol.
012, 2, 406−414.
11) Applying Noyori’s [Ru(S,S)-TsDPEN(p-cym)] (S/C = 1000) at
6
(
(
(
0 °C culminated after 6 h in <10% conversion to cis-A1.
12) For selected recent articles and reviews on DKR−ATH, see:
a) Vyas, V. K.; Bhanage, B. M. Org. Lett. 2016, 18, 6436−6439.
b) Echeverria, P.-G.; Ayad, T.; Phansavath, P.; Ratovelomanana-Vidal,
V. Synthesis 2016, 48, 2523−2539. (c) Cotman, A. E.; Cahard, D.;
D
Org. Lett. XXXX, XXX, XXX−XXX