Reduction of Activated Carbonyl Groups
[4]
For reviews, see: a) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res.
2001, 34, 535; b) B. J. Cowen, J. S. Miller, Chem. Soc. Rev. 2009,
38, 3102; c) J. L. Methot, W. R. Roush, Adv. Synth. Catal.
2004, 346, 1035; d) Y. Wei, M. Shi, Acc. Chem. Res. 2010, 43,
1005; e) C. Nising, S. Bräse, Chem. Soc. Rev. 2008, 37, 1218; f)
L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37, 1140; g)
A. Marinetti, A. Voituriez, Synlett 2010, 174.
W. Zhang, M. Shi, Chem. Commun. 2006, 1218–1220.
M. Shi, X.-G. Liu, Y.-W. Guo, W. Zhang, Tetrahedron 2007,
63, 12731–12734.
Supporting Information (see footnote on the first page of this arti-
cle): Spectroscopic data and computational details are available.
Acknowledgments
We thank the Shanghai Municipal Committee of Science and Tech-
nology (11JC1402600), the National Basic Research Program of
China (973)-2009CB825300, and the National Natural Science
Foundation of China for financial support (21072206, 20472096,
20872162, 20672127, 20821002, and 20732008).
[5]
[6]
[7]
S.-H. Cao, X.-C. Zhang, Y. Wei, M. Shi, Eur. J. Org. Chem.
2011, 2668–2672.
[8] R. T. Li, S. T. Nguyen, R. H. Grubbs, J. W. Ziller, J. Am. Chem.
Soc. 1994, 116, 10032.
[9] Y. Wei, B. Sateesh, B. Maryasin, G. N. Sastry, H. Zipse, J. Com-
put. Chem. 2009, 30, 2617–2624.
[1] For reviews on the Wittig reaction, see: a) B. E. Maryanoff,
A. B. Reitz, Chem. Rev. 1989, 89, 863–927; b) P. J. Murphy, J.
Brennan, Chem. Soc. Rev. 1988, 17, 1–30; c) D. W. Allen, J. C.
Tebby, N. Bricklebank, Organophosphorus Chem. 2003, 33,
289–320.
[10] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria,
M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven,
K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tom-
asi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega,
G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota,
R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda,
O. Kitao, M. J. Frisch, H. Nakai, M. Klene, X. Li, J. E. Knox,
H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gom-
perts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C.
Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A.
Voth, P. Salvador, J. J. Dannengerg, V. G. Zakrzewski, S. Dap-
prich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick,
A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q.
Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov,
G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin,
D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayak-
kara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen,
M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, rev. D.01,
Gaussian, Inc., Wallingford, CT, 2004.
[2] a) H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635–646;
for selected references on the application of the Staudinger re-
action, see: b) E. C. Lee, B. L. Hodous, E. Bergin, C. Shih,
G. C. Fu, J. Am. Chem. Soc. 2005, 127, 11586–11587; c) Y.
Liang, L. Jiao, S. Zhang, J. Xu, J. Org. Chem. 2005, 70, 334–
337; d) J. Li, H.-N. Chen, H. Chang, J. Wang, C.-W. T. Chang,
Org. Lett. 2005, 7, 3061–3064; e) P. T. Nyffeler, C.-H. Liang,
K. M. Koeller, C.-H. Wong, J. Am. Chem. Soc. 2002, 124,
10773–10778; for reviews, see: f) O. Mitsunobu, Synthesis 1981,
1–28; g) D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127–
164; for selected papers, see h) T. Watanabe, I. Gridnev, T. Im-
amoto, Chirality 2000, 12, 346–351; i) G. K. S. Prakash, S.
Chacko, S. Alconcel, T. Stewart, T. Mathew, G. A. Olah, An-
gew. Chem. 2007, 119, 5021; Angew. Chem. Int. Ed. 2007, 46,
4933–4936; j) C. Ahn, R. Correia, P. DeShong, J. Org. Chem.
2002, 67, 1751–1753; k) J. M. Keith, L. Gomez, J. Org. Chem.
2006, 71, 7113–7116.
[3] A. Börner, Phosphorus Ligands in Asymmetric Catalysis, Wiley-
VCH, Weinheim, Germany, 2008.
Received: January 9, 2012
Published Online: March 7, 2012
Eur. J. Org. Chem. 2012, 2386–2393
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
2393