Exploring Structural Diversity in Ligand Design
FULL PAPERS
(3H, m, ArH), 4.78 (1H, d, J=4.9 Hz, CHOH), 3.75 (1H,
ddd, J=4.9 Hz, J=7.1 Hz, J=12.3 Hz, CHNR2), 3.10 (2H,
bs, CHNCH2CH2), 2.99 (1H, dd, J=11.6 Hz, J=14.6 Hz,
CHH), 2.89 (1H, dd, J=7.1 Hz, J=14.6 Hz, CHH), 2.07
(6H, m, 3 CH2), 1.64 (6H, m, 3 CH2), 1.6 (1H, br s, OH);
13C NMR (CDCl3, 100.6 MHz): d=142.9 (C), 141.9 (C),
128.8 (CH), 126.9 (CH), 125.9 (CH), 124.8 (CH), 71.5 (CH),
62.5 (CH), 49.3 (CH), 33.8 (CH2), 28.5 (CH2), 27.0 (CH2),
20.5 (4 CH2); HR-MS (ESI+): m/z=258.1863, calcd. for
C17H24NO [M+H]+: 258.1852.
prehensive Asymmetric Catalysis, Vol. II, (Eds.: E. N.
Jacobsen, A. Pfaltz, H. Yamamoto), Springer-Verlag,
Berlin, 1999, pp 649–677.
[6] a) M. Hoogenraad, G. M. Klaus, N. Elders, S. M. Hooij-
schuur, B. McKay, A. A. Smith, E. W. P. Damen, Tetra-
hedron: Asymmetry 2004, 15, 519; b) M. P. Sibi, L. M.
Stanley, Tetrahedron: Asymmetry 2004, 15, 3353; c) J.
Mao, B. Wan, F. Wu, S. Lu, Tetrahedron Lett. 2005, 46,
7341.
[7] For an enzymatic resolution to afford all four stereoiso-
mers of the aminoindanol scaffold, see: A. Luna, A.
Maestro, C. Astorga, V. Gotor, Tetrahedron: Asymme-
try 1999, 10, 1969.
[8] a) L. Bernardi, B. F. Bonini, M. Comes-Franchini, M.
Fochi, G. Mazzanti, A. Ricci, G. Carchi, Eur. J. Org.
Chem. 2002, 16, 2776; b) D. Zhao, C.-Y. Chen, F. Xu,
L. Tan, R. Tillyer, M. E. Pierce, J. R. Moore, Org.
Synth. 2000, 77, 12.
Supporting Information
Detailed experimental procedures for the preparation of the
enantiopure aminoindanol precursors and ligands derived
from them, as well as the application of these compounds in
asymmetric catalysis are available in the Supporting Infor-
mation.
[9] Y. Hirata, I. Yanagisawa, M. Takeda, H. Ino, K. Taka-
hashi, M. Murakami, Chem. Pharm. Bull. 1977, 25,
1060.
Acknowledgements
[10] D. Zhao, C.-Y. Chen, F. Xu, L. Tan, R. Tillyer, M. E.
Pierce, J. R. Moore, Org. Synth. 2000, 77, 12.
This work was funded by MEC (Grant CTQ2005–02193/
BQU), DIUE (Grant 2005SGR225), Consolider Ingenio
2010 (Grant CSD2006–0003) and ICIQ Foundation.
[11] E. J. Corey, T. D. Roper, K. Ishihara, G. Sarakinos, Tet-
rahedron Lett. 1993, 34, 8399.
[12] G. Desimoni, G. Faita, G. Mellerio, P. P. Righetti, C.
Zanelli, Gazz. Chim. It. 1992, 122, 269.
[13] a) E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker,
L. Deng, J. Am. Chem. Soc. 1991, 113, 7063; b) M. Pal-
ucki, G. J. McCormick, E. N. Jacobsen, Tetrahedron
Lett. 1995, 36, 5457.
[14] M. J. Palmer, J. A. Kenny, T. Walsgrove, A. M. Kawa-
moto, M. Wills, J. Chem. Soc. Perkin Trans. 1 2002, 416.
[15] J. Freedman, M. J. Vaal, E. W. Huber, J. Org. Chem.
1991, 56, 670.
[16] Alkylzinc addition to aldehydes: a) L. Solà, K. S.
Reddy, A. Vidal-Ferran, A. Moyano, M. A. Pericàs, A.
Riera, A. Alvarez-Larena, J.-F. Piniella, J. Org. Chem.
1998, 63, 7078; b) K. S. Reddy, L. Solà, A. Moyano,
M. A. Pericàs, A. Riera, J. Org. Chem. 1999, 64, 3969;
c) K. S. Reddy, L. Solà, A. Moyano, M. A. Pericàs, A.
Riera, Synthesis 2000, 165; d) N. García-Delgado, M.
Fontes, M. A. Pericàs, A. Riera, X. Verdaguer, Tetrahe-
dron: Asymmetry 2004, 15, 2085; e) S. Rodríguez-Es-
crich, K. S. Reddy, C. Jimeno, G. Colet, C. Rodríguez-
Escrich, L. Solà, A. Vidal-Ferran, M. A. Pericàs, J. Org.
Chem. 2008, 73, 5340–5353.
[17] Arylzinc addition to aldehydes: M. Fontes, X. Verda-
guer, L. Solà, M. A. Pericàs, A. Riera, J. Org. Chem.
2004, 69, 2532.
[18] B. Di Simone, D. Savoia, E. Tagliavini, A. Umani-
Ronchi, Tetrahedron: Asymmetry 1995, 6, 301.
[19] C. Boga, F. Manescalchi, D. Savoia, Tetrahedron 1994,
50, 4709.
[20] Crystals of 6b could be obtained by slow evaporation
of a solution of the compound in a mixture of ethanol
and ethyl acetate. Crystal data for 6b at 100 K:
2·(C17H23NO2), 546.73 gmolÀ1, orthorhombic, P212121,
a=6.7084(3) , b=19.3348(9) , c=22.5361(10) ,
V=2923.1(2 3, Z=4, 1calcd. =1.242 Mg/m3, R1 =0.0420
(0.0470), wR2=0.1144 (0.1196), for 16172 reflections
with I>2s(I) (for 17104 reflections [Rint: 0.0250] with a
References
[1] a) A. Vidal-Ferran, A. Moyano, M. A. Pericàs, A.
Riera, Tetrahedron Lett. 1997, 38, 8773–8776; b) A.
Vidal-Ferran, A. Moyano, M. A. Pericàs, A. Riera, J.
Org. Chem. 1997, 62, 4970–4982; c) C. Jimeno, M.
Pastó, A. Riera, M. A. Pericàs, J. Org. Chem. 2003, 68,
3130–3138; d) A. K. Ghosh, S. Fidanze, C. H. Sena-
nayake, Synthesis 1998, 937; e) C. H. Senanayake, Al-
drichimica Acta 1998, 31, 3; f) C. H. Senanayake, E. N.
Jacobsen, in: Process Chemistry in the Pharmaceutical
Industry, (Ed.: K. G. Gadamasetti), Marcel Dekker,
New York, 1999, Vol. 18, p 327.
[2] a) L. Solà, A. Vidal-Ferran, A. Moyano, M. A. Pericàs,
A. Riera, Tetrahedron: Asymmetry 1997, 8, 1559;
b) Corrigendum: L. Solà, A. Vidal-Ferran, A. Moyano,
M. A. Pericàs, A. Riera, Tetrahedron: Asymmetry 1997,
8, 3985.
[3] A. H. Lipkus, Q. Yuan, K. A. Lucas, S. A. Funk, W. F.
Bartelt III, R. J. Schenck, A. J. Trippe, J. Org. Chem.
2008, 73, 4443.
[4] a) C. H. Senanayake, D. Krishnamurthy, I. Gallou, in:
Handbook of Chiral Fine Chemicals, (Ed.: D. Ager),
Taylor Francis, New York, 2005, p 117; b) C. H. Sena-
nayake, D. Krishnamurthy, I. Gallou, in: Handbook of
Chiral Fine Chemicals, (Ed.: D. Ager), Taylor Francis,
New York, 2005, p 319; c) C. H. Senanayake, D. Krish-
namurthy, I. Gallou, in Handbook of Chiral Fine
Chemicals, (Ed.: D. Ager), Taylor Francis, New York,
2005, p 457; d) I. Gallou, C. H. Senanayake, Chem. Rev.
2006, 106, 2843.
[5] a) E. N. Jacobsen, in: Catalytic Asymmetric Synthesis,
(Ed.: I. Ojima), VCH Publishers, New York, 1993,
pp 1159–1202; b) E. N. Jacobsen, M. H. Wu, in: Com-
Adv. Synth. Catal. 2008, 350, 2250 – 2260
ꢀ 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2259