approach as a novel metal-free tool for the synthesis of molecular
therapeutics.9
B. Ramachary, M. Shiva Prasad and R. Madhavachary, Org. Biomol.
Chem., 2011, 9, 2715–2721. For selected papers on asymmetric cascade
reactions from other groups, see: (i) B. Tan, N. R. Candeias and C.
F. Barbas III, Nat. Chem., 2011, 3, 473–477; (j) J. W. Yang, M. T.
Hechavarria Fonseca and B. List, J. Am. Chem. Soc., 2005, 127, 15036–
15037; (k) Y. Huang, A. M. Walji, C. H. Larsen and D. W. C. MacMillan,
J. Am. Chem. Soc., 2005, 127, 15051–15053; (l) M. Marigo, T. Schulte,
J. Franzen and K. A. Jørgensen, J. Am. Chem. Soc., 2005, 127, 15710–
15711; (m) D. Enders, M. R. M. Huettl, C. Grondal and G. Raabe,
Nature, 2006, 441, 861–863;(n) W. Wang, H. Li, J. Wang and L. Zu, J. Am.
Chem. Soc., 2006, 128, 10354–10355; (o) M. Rueping, A. P. Antonchick
and T. Theissmann, Angew. Chem., Int. Ed., 2006, 45, 3683–3686; (p) H.
Ishikawa, T. Suzuki and Y. Hayashi, Angew. Chem., Int. Ed., 2009, 48,
1304–1307; (q) D. Zhu, M. Lu, P. J. Chua, B. Tan, F. Wang, X. Yang and
G. Zhong, Org. Lett., 2008, 10, 4585–4588.
4 (a) D. R. Schroender and F. R. Stermitz, Tetrahedron, 1985, 41, 4309–
4320; (b) J. N. Xiang, P. Nambi, E. H. Ohlstein and J. D. Elliott, Bioorg.
Med. Chem., 1998, 6, 695–700; (c) D. R. Zitsane, I. T. Ravinya, I. A.
Riikure, Z. F. Tetere, E. Y. Gudrinietse and U. O. Kalei, Russ. J. Org.
Chem., 1999, 35, 1457–1460; (d) D. R. Zitsane, I. T. Ravinya, I. A.
Riikure, Z. F. Tetere, E. Y. Gudrinietse and U. O. Kalei, Russ. J. Org.
Chem., 2000, 36, 496–501; (e) D. Pizzirani, M. Roberti, S. Grimaudo, A.
Di Cristina, R. M. Pipitone, M. Tolomeo and M. Recanatini, J. Med.
Chem., 2009, 52, 6936–6940.
5 For the recent papers on Barbas dienamines, see: (a) D. B. Ramachary,
N. S. Chowdari and C. F. Barbas III, Angew. Chem., Int. Ed., 2003,
42, 4233–4237; (b) D. B. Ramachary, K. Anebouselvy, N. S. Chowdari
and C. F. Barbas III, J. Org. Chem., 2004, 69, 5838–5849; (c) D. B.
Ramachary and C. F. Barbas III, Chem.–Eur. J., 2004, 10, 5323–5331;
(d) D. B. Ramachary and C. F. Barbas III, Org. Lett., 2005, 7, 1577–1580;
(e) F. Aznar, A.-B. Garc´ıa and M.-P. Cabal, Adv. Synth. Catal., 2006,
348, 2443–2448; (f) N. Momiyama, Y. Yamamoto and H. Yamamoto, J.
Am. Chem. Soc., 2007, 129, 1190–1195; (g) D. B. Ramachary, Y. V. Reddy
and B. V. Prakash, Org. Biomol. Chem., 2008, 6, 719–726; (h) B. Jiang,
W.-J. Hao, J.-P. Zhang, S.-J. Tu and F. Shi, Org. Biomol. Chem., 2009, 7,
2195–2201; (i) L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G.
Bartoli and P. Melchiorre, Angew. Chem., Int. Ed., 2009, 48, 7196–7199;
(j) G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli,
M.-P. Song, G. Bartoli and P. Melchiorre, Angew. Chem., Int. Ed., 2009,
48, 7200–7203.
Acknowledgements
This work was made possible by a grant from the Depart-
ment of Science and Technology (DST), New Delhi [Grant
No.: DST/SR/S1/OC-65/2008]. SB would like to thank DBT
(BT/PR10092/BRB/10/585/2007 letter-II) and DST-PURSE
for financial assistance. YVR and AB thank Council of Scientific
and Industrial Research (CSIR), New Delhi for their research
fellowship. We thank Dr P. Raghavaiah for his help in X-ray
structural analysis.
Notes and references
1 For recent reviews on organocatalytic cascade and sequential one-pot
combination of MCR/MCC reactions, see: (a) W. Notz, F. Tanaka and
C. F. Barbas III, Acc. Chem. Res., 2004, 37, 580–591; (b) J. Seayad and
B. List, Org. Biomol. Chem., 2005, 3, 719–724; (c) G. Lelais and D.
W. C. McMillan, Aldrichim. Acta, 2006, 39, 79–87; (d) D. J. Ramon
and M. Yus, Angew. Chem., Int. Ed., 2005, 44, 1602–1634; (e) H.-C.
Guo and J.-A. Ma, Angew. Chem., Int. Ed., 2006, 45, 354–366; (f) H.
Pellissier, Tetrahedron, 2006, 62, 2143–2173; (g) C. J. Chapman and C.
G. Frost, Synthesis, 2007, 1–21; (h) G. Guillena, D. J. Ramon and M. Yus,
Tetrahedron: Asymmetry, 2007, 18, 693–700; (i) D. Enders, C. Grondal
and M. R. M. Huettl, Angew. Chem., Int. Ed., 2007, 46, 1570–1581;
(j) A. Erkkila¨, I. Majander and P. M. Pihko, Chem. Rev., 2007, 107,
5416–5470; (k) S. Bertelsen and K. A. Jørgensen, Chem. Soc. Rev., 2009,
38, 2178–2189; (l) B. Westermann, M. Ayaz and S. S. van Berkel, Angew.
Chem., Int. Ed., 2010, 49, 846–849; (m) D. B. Ramachary and S. Jain,
Org. Biomol. Chem., 2011, 9, 1277–1300; (n) M. Rueping, J. Dufour and
F. R. Schoepke, Green Chem., 2011, 13, 1084–1105; (o) A. M. Walji
and D. W. C. MacMillan, Synlett, 2007, 1477–1489; (p) C. Grondal, M.
Jeanty and D. Enders, Nat. Chem., 2010, 2, 167–178; For recent reviews
on general cascade reactions, see: (q) L. F. Tietze, Chem. Rev., 1996,
96, 115–136; (r) L. F. Tietze and A. Modi, Med. Res. Rev., 2000, 20,
304–322; (s) K. C. Nicolaou, T. Montagnon and S. A. Snyder, Chem.
Commun., 2003, 551–564.
6 CCDC-828199 for cis-(-)-1gab and CCDC-828200 for cis-(-)-1gcb
contains the supplementary crystallographic data for this paper. See
the ESI for crystal structures†.
7 For reviews discussing the influence of electrostatic effects on facial
selectivities, see: (a) G. Mehta and J. Chandrasekhar, Chem. Rev., 1999,
99, 1437–1468; (b) P. Wipf and J. Jung, Chem. Rev., 1999, 99, 1469–1480.
For attractive non-covalent interactions in asymmetric organocatalysis,
see: (c) C. Allemann, R. Gordillo, F. R. Clemente, P. H. Cheong and
K. N. Houk, Acc. Chem. Res., 2004, 37, 558–569; (d) J. Joseph, D.
B. Ramachary and E. D. Jemmis, Org. Biomol. Chem., 2006, 4, 2685–
2689; (e) R. R. Knowles and E. N. Jacobsen, Proc. Natl. Acad. Sci. U. S.
A., 2010, 107, 20678–20685; (f) S. Yamada and J. S. Fossey, Org. Biomol.
Chem., 2011, 9, DOI: 10.1039/c1ob05228d; (g) A. K. Sharma and R. B.
Sunoj, Chem. Commun., 2011, 47, 5759–5761.
2 E. E. Shults, E. A. Semenova, A. A. Johnson, S. P. Bondarenko, I. Y.
Bagryanskaya, Y. V. Gatilov, G. A. Tolstikov and Y. Pommier, Bioorg.
Med. Chem. Lett., 2007, 17, 1362–1368.
3 For selected recent papers on asymmetric cascade reactions from our
group, see: (a) D. B. Ramachary and M. Kishor, J. Org. Chem., 2007, 72,
5056–5068; (b) D. B. Ramachary and R. Sakthidevi, Org. Biomol. Chem.,
2008, 6, 2488–2492; (c) D. B. Ramachary and M. Kishor, Org. Biomol.
Chem., 2008, 6, 4176–4187; (d) D. B. Ramachary and R. Sakthidevi,
Chem.–Eur. J., 2009, 15, 4516–4522; (e) D. B. Ramachary and Y. V.
Reddy, J. Org. Chem., 2010, 75, 74–85; (f) D. B. Ramachary and M.
Kishor, Org. Biomol. Chem., 2010, 8, 2859–2867; (g) D. B. Ramachary
and R. Sakthidevi, Org. Biomol. Chem., 2010, 8, 4259–4265; (h) D.
8 S. Broder, Antiviral Res., 2010, 85, 1–18.
9 M. J. Gaunt, C. C. C. Johansson, A. McNally and N. T. Vo, Drug
Discovery Today, 2007, 12, 8–27.
7286 | Org. Biomol. Chem., 2011, 9, 7282–7286
This journal is
The Royal Society of Chemistry 2011
©