Organic & Biomolecular Chemistry
Paper
33, 61; (b) M. V. R. Reddy, H. C. Brown and
P. V. Ramachandran, J. Organomet. Chem., 2001, 624, 239;
(c) N. Andrushko, V. Andrushko, V. Tararov, A. Korostylev,
G. König and A. Börner, Chirality, 2010, 22, 534;
(d) P. Sawant and M. E. Maier, Tetrahedron, 2010, 66, 9738;
(e) W. Fan, W. Li, X. Ma, X. Tao, X. Li, Y. Yao, X. Xie and
Z. Zhang, J. Org. Chem., 2011, 76, 9444; (f) L. Hu, F. Xiong,
X. Chen, W. Chen, Q. He and F. Chen, Tetrahedron: Asym-
metry, 2013, 24, 207.
8 (a) D. E. Butler, C. F. Deering, A. Millar, T. N. Nanninga
and B. D. Roth, PCT Int. Appl. WO 8907598, 1989;
(b) H. Shin, B. S. Choi, K. K. Lee, H. Choi, J. H. Chang,
K. W. Lee, D. H. Nam and N. S. Kim, Synthesis, 2004, 2629;
(c) P. P. Reddy, K. F. Yen and B. J. Uang, J. Org. Chem., 2002,
67, 1034; (d) V. Tararov, G. König and A. Börner, Adv. Synth.
Catal., 2006, 348, 2633.
9 P. J. Harrington, Lipitor (Atorvastatin Calcium), Chapter 9,
in Pharmaceutical Process Chemistry for Synthesis: Rethinking
the Routes to Scale-Up, Wiley & Sons, New York, 2011,
pp. 294–359.
10 (a) Y. Kawato, M. Iwata, R. Yazaki, N. Kumagai and
M. Shibasaki, Tetrahedron, 2011, 67, 6539; (b) Y. Kawato,
S. Chaudhary, N. Kumagai and M. Shibasaki, Chem. – Eur. J.,
2013, 19, 3802.
Acknowledgements
The authors wish to thank CNPq (INCT-INOFAR Grant CNPq
573.564/2008–6 and FAPERJ E-26/170.020/2008), Cristália Pro-
dutos Químicos Farmacêuticos, and FAPESP (process number
2012/02230-0) for their financial support.
Notes and references
1 (a) B. D. Roth and A. A. Mich, U.S. Patent 4681893, 1987;
(b) B. D. Roth, C. J. Blankley, A. W. Chucholowski,
E. Ferguson, M. L. Hoefle, D. F. Ortwine, R. S. Newton,
C. S. Sekerke, D. R. Sliskovic, C. D. Stratton and
M. W. Wilson, J. Med. Chem., 1991, 34, 357; (c) B. D. Roth
and A. A. Mich, U.S. Patent 5273995, 1991; (d) A. Endo,
J. Lipid Res., 1992, 33, 1569; (e) M. Hajkova, B. Kratochvil
and S. Radl, Chem. Listy, 2008, 102, 2.
2 Z. Casar, Curr. Org. Chem., 2010, 14, 816.
3 M. Braun and R. Devant, Tetrahedron Lett., 1984, 25,
5031.
4 (a) P. L. Brower, D. E. Butler, C. F. Deering, T. V. Le,
A. Millar, T. N. Nanninga and B. D. Roth, Tetrahedron Lett.,
1992, 33, 2279; (b) K. L. Baumann, D. E. Butler,
C. F. Deering, K. E. Mennen, A. Millar, T. N. Nanninga, 11 For seminal work, see: (a) M. A. Blanchette, M. S. Malamas,
C. W. Palmer and B. D. Roth, Tetrahedron Lett., 1992, 33,
2283.
M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour,
S. Masamune, M. Kageyama and T. Tamura, J. Org. Chem.,
1989, 54, 2817. For fundamental contributions in this area,
see: (b) I. Paterson, R. M. Oballa and R. D. Norcross,
Tetrahedron Lett., 1996, 37, 8581; (c) I. Paterson,
K. R. Gibson and R. M. Oballa, Tetrahedron Lett., 1996, 37,
8585; (d) D. A. Evans, P. J. Coleman and B. Côté, J. Org.
Chem., 1997, 62, 788; (e) D. A. Evans, B. Côté, P. J. Coleman
and B. T. Connell, J. Am. Chem. Soc., 2003, 125,
10893.
5 (a) M. Müller, Angew. Chem., Int. Ed., 2005, 44, 362;
(b) A. R. Moen, B. H. Hoff, L. K. Hansen, T. Anthonsen and
E. E. Jacobsen, Tetrahedron: Asymmetry, 2004, 15, 1551;
(c) J. M. Patel, J. Mol. Catal. B: Enzym., 2009, 61, 123;
(d) H. Asako, M. Shimizu and N. Itoh, Appl. Microbiol. Bio-
technol., 2009, 84, 397.
6 (a) X. Chen, F. Xiong, W. Chen, Q. He and F. Chen, J. Org.
Chem., 2014, 79, 2723; (b) J. M. Lopchuk and G. W. Gribble,
Tetrahedron Lett., 2015, 56, 3208; (c) J. Liu, C. C. Hsu and 12 For our recent work in this area, see: (a) L. C. Dias,
C. H. Wong, Tetrahedron Lett., 2004, 45, 2439;
(d) S. Bergeron, D. A. Chaplin, J. H. Edwards, B. S. W. Ellis,
C. L. Hill, K. Holt-Tiffin, J. R. Knight, T. Mahoney,
A. P. Osborne and G. Ruecroft, Org. Process Res. Dev., 2006,
10, 661; (e) R. Öhrlein and G. Baisch, Adv. Synth. Catal.,
2003, 345, 713; (f) W. A. Greenberg, A. Varvak,
S. R. Hanson, K. Wong, H. Huang, P. Chen and M. J. Burk,
Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 5788;
(g) S. Goldberg, Z. Guo, S. Chen, A. Goswami and
R. N. Patel, Enzyme Microb. Technol., 2008, 43, 544;
(h) X. Wu, L. Wang, S. Wang and Y. Chen, Amino Acids,
2010, 39, 305; (i) X. Wu, J. Jiang and Y. Chen, ACS Catal.,
2011, 1, 1661; ( j) F. Sun, G. Xu, J. Wu and L. Yang, Tetra-
hedron: Asymmetry, 2007, 18, 2454; (k) S. Ma, J. Gruber,
C. Davis, L. Newman, D. Gray, A. Wang, J. Grate,
G. W. Huisman and R. A. Sheldon, Green Chem., 2010,
12, 81.
A. A. Marchi, M. A. B. Ferreira and A. M. Aguilar, Org. Lett.,
2007, 9, 4869; (b) L. C. Dias and A. M. Aguilar, Quím. Nova,
2007, 30, 2007; (c) L. C. Dias, A. A. Marchi, M. A. B. Ferreira
and A. M. Aguilar, J. Org. Chem., 2008, 73, 6299;
(d) L. C. Dias and A. M. Aguilar, Chem. Soc. Rev., 2008, 37,
451; (e) L. C. Dias, S. M. Pinheiro, V. M. de Oliveira,
M. A. B. Ferreira, C. F. Tormena, A. M. Aguilar,
J. Zukerman-Schpector and E. R. T. Tiekink, Tetrahedron,
2009, 65, 8714; (f) L. C. Dias, E. C. de Lucca Jr.,
M. A. B. Ferreira, D. C. Garcia and C. F. Tormena, Org. Lett.,
2010, 12, 5056; (g) L. C. Dias, E. C. de Lucca Jr.,
M. A. B. Ferreira, D. C. Garcia and C. F. Tormena, J. Org.
Chem., 2012, 77, 1765; (h) L. C. Dias, E. C. Polo,
M. A. B. Ferreira and C. F. Tormena, J. Org. Chem., 2012,
77, 3766. For theoretical studies, see: (i) R. S. Paton and
J. M. Goodman, Org. Lett., 2006, 8, 4299; ( j) J. M. Goodman
and R. S. Paton, Chem. Commun., 2007, 2124; (k) R. S. Paton
and J. M. Goodman, J. Org. Chem., 2008, 73, 1253.
7 (a) H. Jendralla, E. Baader, W. Bartmann, G. Beck,
A. Bergmann, E. Granzer, B. V. Kerekjarto, K. Kesseler, 13 R. R. Sagyam, H. Vurimidi, P. R. Padi and M. R. Ghanta,
R. Krause, W. Schubert and G. Wess, J. Med. Chem., 1990,
J. Heterocycl. Chem., 2007, 44, 923.
This journal is © The Royal Society of Chemistry 2016
Org. Biomol. Chem.