Gui-Ling Zhao et al.
COMMUNICATIONS
T. Ohta, J. S. Cleere, P. A. Marsella, Science 1976, 193,
542.
rera, M. Marigo, K. A. Jørgensen, Angew. Chem. Int.
Ed. 2007, 46, 1101; m) D. Enders, M. R. M. Hüttl, J.
Runsink, J.; Raabe, B. Wendt, Angew. Chem. Int. Ed.
2007, 46, 467; n) M. Marigo, S. Bertelsen, A. Landa,
K. A. Jørgensen, J. Am. Chem. Soc. 2006, 128, 5475;
o) R. Rios, H. SundØn, J. Vesely, G. L. Zhao, P. Dziedz-
ic, A. Córdova, Adv. Synth. Cat. 2007, 349, 1028; p) T.
Govender, L. Hojabri, F. M. Moghaddam, P. I. Arvids-
son, Tetrahedron: Asymmetry 2006, 17, 1763; q) H.
SundØn, I. Ibrahem, G. L. Zhao, L. Eriksson, A. Córdo-
va, Chem. Eur. J. 2007, 13, 574; r) D. Enders, A. A.
Narine, T. R. Benninghaus, G. Raabe, Synlett 2007,
1667.
[5] a) P. T. Kaye, S. Afr. J. Sciences 2004, 100, 545; b) P. T.
Kaye, X. W. Nocanda, Synthesis 2001, 2389; see also:
c) J. TØrcio, B. Ferreira, V. Catani, J. V. Comasseto,
Synthesis 1987, 149; d) A. Arnoldi, M. Carughi, Synthe-
sis 1998, 155; e) K. Kobayashi, H. Konishi, T. Kitamura,
O. Morikawa, R. Nakahashi, J. Chem. Soc., Perkin
Trans; 1 1999, 1547; f) G. V. Nenajdenko, A. V. Sanin,
A. V. Churakov, J. A. K. Howard, E. S. G. Balenkova,
Chem. Heterocycl. Compd. 1999, 35, 549; g) H. Sunden,
I. Ibrahem, R. Rios, G.-L. Zhao, A. Córdova, A.
Chemia 2007, 61, 219.
[6] For reviews on this concept see: a) L. F. Tietze, G. Bra-
sche, K. Gericke, Domino Reactions in Organic Synthe-
sis, Wiley-VCH, Weinheim 2006, p 672; b) L. F. Tietze,
Chem. Rev. 1996, 96, 115; c) K. C. Nicolaou, D. J. Ed-
monds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45,
7134; d) H. Guo, J. Ma, Angew. Chem. Int. Ed. 2006,
45, 354; e) H. Pellissier, Tetrahedron 2006, 62, 2143;
f) D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005,
44, 1602.
[11] a) W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc.
2006, 128, 10354; b) R. Rios, H. Sunden, I. Ibrahem, G.
L. Zhao, L. Eriksson, A. Córdova, Tetrahedron Lett.
2006, 47, 8547; c) For a recent thiourea-catalyzed syn-
thesis see: L. Zu, J. Wang, H. Li, H. Xie, W. Jiang, W.
Wang, J. Am. Chem. Soc. 2007, 129, 1036; d) for 2-mer-
capto-1-phenyl ethanones as nucleophildes see: S.
Brandau, E. Maerten, K. A. Jørgensen, J. Am. Chem.
Soc. 2006, 128, 14986.
[7] a) B. M. Trost, Science 1991, 254, 1471; b) B. M. Trost,
Angew. Chem. Int. Ed. 1995, 107, 258.
[12] R. Rios, H. SundØn, I. Ibrahem, A. Córdova, Tetrahe-
dron Lett. 2007, 48, 2181.
[8] a) P. T. Anastas, J. C. Warner, Green Chemistry: Theory
and Practice, Oxford University Press, Oxford, 2000,
p 135; b) for an excellent paper on combining one-pot,
step reduction and atom economy in organic chemistry,
see: P. A. Clarke, S. Santos, W. H. C. Martin, Green
Chem. 2007, 9, 438.
[9] For a review on organocatalytic domino reactions see:
a) D. Enders, C. Grondal, M. R. M. Hüttl, Angew.
Chem. Int. Ed. 2007, 46, 1570; for selected reviews on
organocatalysis see: b) P. I. Dalko, L. Moisan, Angew.
Chem. Int. Ed. 2001, 40, 3726; c) B. List, Chem.
Commun. 2006, 819; d) P. I. Dalko, L. Moisan, L.
Angew. Chem. Int. Ed. 2004, 43, 5138; e) M. Marigo,
K. A. Jørgensen, Chem. Commun. 2006, 2001.
[10] For selected examples of organocatalytic asymmetric
domino reactions see: a) N. Halland, P. S. Aburell,
K. A. Jørgensen, Angew. Chem. Int. Ed. 2004, 43, 1272;
b) Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. Mac-
Millan, J. Am. Chem. Soc. 2005, 127, 15051; c) J. W.
Yang, M. T. Hechavarria Fonseca, B. List, J. Am.
Chem. Soc. 2005, 127, 15036; d) M. Marigo, T. Schulte,
J. FranzØn, K. A. Jørgensen, J. Am. Chem. Soc. 2005,
127, 15710; e) Y. Yamamoto, N. Momiyama, H. Yama-
moto, J. Am. Chem. Soc. 2004, 126, 5962; f) D. B. Ram-
achary, N. S. Chowdari, C. F. Barbas III, Angew. Chem.
Int. Ed. 2003, 42, 4233; g) M. Marigo, J. FranzØn, T. B.
Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem.
Soc. 2005, 127, 6964; h) H. SundØn, I. Ibrahem, L.
Eriksson, A. Córdova, Angew. Chem. Int. Ed. 2005, 44,
4877; i) D. Enders, M. R. M. Hüttl, C. Grondal, G.
Raabe, Nature 2006, 441, 861; j) H. SundØn, I. Ibrahem,
A. Córdova, Tetrahedron Lett. 2006, 47, 99; k) A. Car-
lone, M. Marigo, C. North, A. Landa, K. A. Jørgensen,
Chem. Commun. 2006, 47, 4928; l) A. Carlone, S. Cab-
[13] a) I. Ibrahem. R. Rios, J. Vesely, A. Córdova, Tetrahe-
dron Lett. 2007, 48, 6252; b) J. Vesely, I. Ibrahem. G.-L.
Zhao, R. Rios, A. Córdova, Angew. Chem. Int. Ed.
2007, 46, 778; c) H. SundØn, R. Rios, I. Ibrahem. G.-L.
Zhao, L. Eriksson, A. Córdova, Adv. Synth. Cat. 2007,
349, 827; d) R. Rios, J. Vesely, H. SundØn, I. Ibra-
hem. G. L. Zhao, A. Córdova, Tetrahedron Lett. 2007,
48, 5835.
[14] D. Enders, K. Lüttgen, A. A. Narine, Synthesis 2007,
959.
[15] For an excellent review on the topic of asymmetric
thia-Michael additions see: D. Enders, K. Lüttingen,
A. A. Narine, Synthesis 2007, 959.
[16] Selected examples of the use of protected diarylproli-
nols in catalysis see: a) M. Marigo, T. C. Wabnitz, D.
Fielenbach, K. A. Jørgensen, Angew. Chem. Int. Ed.
2005, 44, 794; b) M. Marigo, D. Fielenbach, A. Braun-
ton, A. Kjaersgaard, K. A. Jørgensen, Angew. Chem.
Int. Ed. 2005, 44, 3703; c) J. FranzØn, M. Marigo, D.
Fielenbach, T. C. Wabnitz, A. Kjaersgaard, K. A. Jør-
gensen, J. Am. Chem. Soc. 2005, 127, 18296; d) Y. Hay-
ashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem.
Int. Ed. 2005, 44, 4212; e) M. Marigo, J. FranzØn, T. B.
Poulsen, W. Zhuang, K. A. Jørgensen, J. Am. Chem.
Soc. 2005, 127, 6964; f) I. Ibrahem, A. Córdova , Chem.
Commun. 2006, 1760; g) Y. Shi, S. H. Gellman, Org.
Lett. 2005, 4253.
[17] The protected diarylprolinol catalyzed reactions be-
tween 2’-aminoacetophenone and enals gave the corre-
sponding optically active Michael adducts under the in-
vestigated reaction conditions.
[18] The enal products can enolize upon isolation by silica
gel chromatography, which can lead to a decrease in
diastereomeric ratio.
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Adv. Synth. Catal. 2008, 350, 237 – 242