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Córdova, A.1
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Selected examples of direct Mannich reactions using unmodified ketones and/or aldehydes as donors: with metal catalysts: a) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083;
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and references therein
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c) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712, and references therein;
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Matsunaga, S.1
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with organocatalysts: d) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
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List, B.1
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e) W. Notz, K. Sakthivel, T. Bui, G. Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199;
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Notz, W.1
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f) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827;
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List, B.1
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g) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842;
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h) A. Córdova, S.-i. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866;
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i) Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805;
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Hayashi, Y.1
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j) W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576;
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and references therein. see reviews in ret. [1]
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k) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356, and references therein. For other related examples, see reviews in ret. [1].
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Uraguchi, D.1
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See refs [1] and [2a-c]; see also a) N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168;
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c) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169.
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3242721636
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For exceptional examples in Mannich-type reactions using readily enolizable substrates with the oxidation state of carboxylic acid, see: with glycine Schiff base as a donor: a) T. Ooi, M. Kameda, J. Fujii, K. Maruoka, Org. Lett. 2004, 6, 2397;
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b) L. Bernardi, R. G. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583;
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Bernardi, L.1
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Jørgensen, K.A.4
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22
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0037495950
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with malonates and ketoesters as donors: c) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359;
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Marigo, M.1
Kjærsgaard, A.2
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Jørgensen, K.A.5
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23
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d) Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem. 2005, 117, 1549;
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Hamashima, Y.1
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Sodeoka, M.6
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25
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0038298158
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Asymmetric aldol reactions: a) D. A. Evans, C. W. Downey, J. L. Hubbs, J. Am. Chem. Soc. 2003, 125, 8706;
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Evans, D.A.1
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b) Y. Suto, N. Kumagai, S. Matsunaga, M. Kanai, M. Shibasaki, Org. Lett. 2003, 5, 3147;
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Suto, Y.1
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27
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0037160423
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diastereoselective aldol reactions: c) D. A. Evans, J. S. Tedrow, J. T. Shaw, C. W. Downey, J. Am. Chem. Soc. 2002, 124, 392;
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Evans, D.A.1
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d) D. A. Evans, C. W. Downey, J. T. Shaw, J. S. Tedrow, Org. Lett. 2002, 4, 1127;
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29
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racemic aldol reactions: e) G. Lalic, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2003, 125, 2852;
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f) N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 13632.
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a) D. A. Evans, G. Borg, K. A. Scheidt, Angew. Chem. 2002, 114, 3320;
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Evans, D.A.1
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for the application of N-acylpyrrole as a donor after conversion into enol silane, see: b) D. A. Evans, D. S. Johnson, Org. Lett. 1999, 1, 595;
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Evans, D.A.1
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c) D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480.
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2942635094
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For the use of an α,β-unsaturated N-acylpyrrole as an electrophile, see: a) S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559;
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1542292774
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b) T. Kinoshita, S. Okada, S. Matsunaga, Park, S.-R. Angew. Chem. 2003, 115, 4828;
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Kinoshita, T.1
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12944296640
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c) T. Mita, K. Sasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 514.
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Mita, T.1
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39
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22744458808
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see the Supporting Information
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For the determination of relative and absolute configurations of Mannich adducts 6a-1, see the Supporting Information.
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40
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0037420322
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The addition of MS 5 Å had beneficial effects on the reaction rate but did not affect the enantiomeric excess. Similar effects of molecular sieves were observed in related reactions using zinc catalysts and hydroxy ketones as donors; see, a) S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582;
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Harada, S.1
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41
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3242668608
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and references therein; see also, refs [2b,c and 3b,c]
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b) S. Matsunaga, T. Yoshida, H. Morimoto, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8777, and references therein; see also, refs [2b,c and 3b,c].
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Matsunaga, S.1
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Shibasaki, M.5
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44
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15944403573
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After submission of this manuscript, an excellent organocatalytic Mannich reaction using α-oxyaldehydes was reported, see: a) I. Ibrahem, A. Córdova, Tetrahedron Lett. 2005, 46, 2839;
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Tetrahedron Lett.
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Ibrahem, I.1
Córdova, A.2
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45
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9144264805
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α-oxyaldehydes were also used as donors in organocatalytic aldol (dimerization) reactions, see: b) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204;
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Northrup, A.B.1
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MacMillan, D.W.C.4
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47
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17644416552
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c) J. Casas, M. Engqvist, I. Ibrahem, B. Kaynak, A. Córdova, Angew. Chem. 2005, 117, 1367;
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Casas, J.1
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48
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14844283105
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and references therein
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Angew. Chem. Int. Ed. 2005, 44, 1343, and references therein;
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Angew. Chem. Int. Ed.
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49
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22744454008
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in press
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for related recent work using α-oxyketones as donors, see also: d) D. Enders, C. Grondal, M. Vrettou, G. Raabe, Angew. Chem. 2005, 117, in press;
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Angew. Chem.
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Enders, D.1
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50
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22744449096
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in press; see refs [1, 2], and references therein
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Angew. Chem. Int. Ed. 2005, 44, in press; for other examples using α-oxyke tones, see refs [1, 2], and references therein.
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(2005)
Angew. Chem. Int. Ed.
, vol.44
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51
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22744438456
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note
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The diastereoselectivity of the reaction with the imine from benzaldehyde was improved by using the bulkier 2,4,6-triisopropylbenzenesulfonyl imine (syn/anti = 78:22, syn: 95% ee); however, reactivity decreased significantly (27% yield).
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52
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22744434324
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see refs [6, 7], and references therein
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For conversion of N-acylpyrrole units, see refs [6, 7], and references therein.
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-
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53
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0002829653
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see ref. [2a]
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For the removal of Ts group using Mg powder, see ref. [2a]; see, also: B. Nyasse, L. Grehn, U. Ragnarsson, Chem. Commun. 1997, 1017.
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Chem. Commun.
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Nyasse, B.1
Grehn, L.2
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0000476716
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a) M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essefeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183;
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Blanchette, M.A.1
Choy, W.2
Davis, J.T.3
Essefeld, A.P.4
Masamune, S.5
Roush, W.R.6
Sakai, T.7
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56
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note
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3 can be purchased from Kojundo Chemical lab (sales@kojundo.co.jp).
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