S. M. Sarkar et al. / Tetrahedron Letters 52 (2011) 923–927
927
6. Initially, we attempted asymmetric intermolecular aldol reactions of N-Boc-4-
piperidone with HCHO, TBSOCH2CHO, and PMBOCH2CHO using -proline (13a),
Acknowledgments
L
13b, and the Xiao’s catalyst. However, all reactions gave the desired aldol
products in very poor yields (<10%). cf. Cordova, A.; Notz, W.; Barbas, C. F., III J.
Org. Chem. 2002, 67, 301–303; Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.;
Urushima, T.; Shoji, M. Angew. Chem., Int. Ed. 2006, 45, 958–961; Chen, J.; Li, X.;
Xing, X.; Xiao, W. J. Org. Chem. 2006, 71, 8198–8202.
This work was partly supported by Grant-in-Aid for the Scien-
tific Research of Japan Society for the Promotion of Science (JSPS)
and The Ministry of Education, Culture, Sports, Science and Tech-
nology (MEXT).
7. Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305–3308.
8. Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42,
2785–2788. and references therein.
Supplementary data
9. (a) Minato, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766–768; (b) von
Riesen, C.; Jones, P. G.; Hoffmann, H. M. R. Chem. Eur. J. 1996, 2, 673–684.
10. Daumas, M.; Vo-Quang, L.; Goffic, F. L.; Vo-Quang, Y. Synthesis 1989, 64–65.
11. For 13b (a) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.;
Shoji, M.; Hashizume, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435–1439;
For 13c (b) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew.
Chem., Int. Ed. 2004, 43, 1983–1986; For 13d (c) Morokuma, K.; Taira, Y.;
Uehara, Y.; Shibahara, S.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron
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Asian J. 2008, 3, 922–948.
Supplementary data (experimental procedures and character-
ization data for all compounds) associated with this article can
References and notes
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