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For synthetic work by Salomon, Burke, and Yonemitsu, see: (a) S. Kim and R. G. Salomon. Tetrahedron Lett. 30, 6279 (1989); A. J. Cooper, W. Pan, R. G. Salomon. Tetrahedron Lett. 34, 8193 (1993) and the references cited therein; (b) S. D. Burke, K. C. Lee, D. Santafianos. Tetrahedron Lett. 32, 3957 (1991); B. C. Austad, A. C. Hart, S. D. Burke. Tetrahedron 58, 2011 (2002) and the references cited therein; (c) K. Horita, S. Hachiya, M. Nagasawa, M. Hikota, O. Yonemitsu. Synlett 38 (1994); K. Horita, M. Nagasawa, Y. Sakurai, O. Yonemitsu. Chem. Pharm. Bull. 46, 1199 (1998) and references cited therein.
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37
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85038477208
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note
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2Mg.
-
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-
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38
-
-
85038467421
-
-
note
-
2 (96%).
-
-
-
-
39
-
-
85038461748
-
-
note
-
An additional benefit was later recognized for this protection; enolization was detected in the series with a MeO group at C31 but not in the series with a BnO group.
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41
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33845280103
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0141712450
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0033550177
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In cyclic systems, allylic and homoallylic alcohols are known to direct the stereochemical course in conjugate additions of Grignard and cuprate reagents. For example, see: F. F. Fleming, J. Guo, Q. Wang, D. Weaver, J. Org. Chem. 64, 8568 (1999) and references cited therein.
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85038456551
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note
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2C≡CH; (4) hydrostannylation, followed by iodination; and (5) trisylation.
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56
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For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
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For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
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Bandini, M.1
Cozzi, P.G.2
Melchiorre, P.3
Umani-Ronchi, A.4
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58
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0035961114
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For asymmetric Cr-mediated allylation, see: (a) K. Sugimoto, S. Aoyagi, C. Kibayashi, J. Org. Chem. 62, 2322 (1997); (b) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi. Angew. Chem. Int. Ed. 38, 3357 (1999) and M. Bandini, P. G. Cozzi, A. Umani-Ronchi. Tetrahedron 57, 835 (2001).
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(2001)
Tetrahedron
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Bandini, M.1
Cozzi, P.G.2
Umani-Ronchi, A.3
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60
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85038461945
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note
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3NCl/THF, and (3) NaH/1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) or 1,1,3,3-tetramethylurea (TMU), were routinely used to screen a ligand. The ratios given in Scheme 8 were obtained under condition 1, whereas those given in Scheme 7 were obtained under condition 3.
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64
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85038456739
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note
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3Al/toluene/-5 °/1 h, RT/14 h, and then -20 °C/1 D for 38.
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65
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0035913709
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A four-centered transition state involving one vinylchromium species was suggested for an intramolecular Ni(II)/Cr(II)-mediated coupling: D. W. C. MacMillan, L. E. Overman, L. D. Pennington. J. Am. Chem. Soc. 123, 9033 (2001) and 117, 10391 (1995).
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J. Am. Chem. Soc.
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MacMillan, D.W.C.1
Overman, L.E.2
Pennington, L.D.3
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66
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0028868420
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A four-centered transition state involving one vinylchromium species was suggested for an intramolecular Ni(II)/Cr(II)-mediated coupling: D. W. C. MacMillan, L. E. Overman, L. D. Pennington. J. Am. Chem. Soc. 123, 9033 (2001) and 117, 10391 (1995).
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J. Am. Chem. Soc.
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67
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33845375339
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For the structure of benzaldehyde/boron trifluoride adduct, see: M. T. Reetz, M. Hullmann, W. Massa, S. Berger, P. Rademacher, P. Heymanns. J. Am. Chem. Soc. 108, 2405 (1986).
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Reetz, M.T.1
Hullmann, M.2
Massa, W.3
Berger, S.4
Rademacher, P.5
Heymanns, P.6
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72
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(a) M. Kuroboshi, M. Tanaka, S. Kishimoto, G. Kentaro, H. Tanaka, S. Torii. Tetrahedron Lett. 40, 2785 (1999);
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Kuroboshi, M.1
Tanaka, M.2
Kishimoto, S.3
Kentaro, G.4
Tanaka, H.5
Torii, S.6
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75
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85038475003
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note
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The rate of coupling was found significantly faster in MeCN than in EtCN. However, the enantioselectivity was significantly lower in MeCN than in EtCN.
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76
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0000499917
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3 is known to possess an unusual square-pyramidal geometry similar to 42: J. J. H. Edema, S. Gambarotta, A. Meetsma, F. van Bolhuis, A. L. Spek, W. J. J. Smeets. Inorg. Chem, 29, 2147 (1990).
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Edema, J.J.H.1
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Van Bolhuis, F.4
Spek, A.L.5
Smeets, W.J.J.6
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77
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85038450139
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note
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2 in several portions (3∼4 x 1 mol %), the homocoupling of 28 could be avoided.
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78
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33847089947
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(a) Y. Okude, S. Hirano, T. Hiyama, H. Nozaki. J. Am. Chem. Soc. 99, 3179 (1977);
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79
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0000346752
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(b) Y. Okude, T. Hiyama, H. Nozaki. Tetrahedron Lett. 43, 3829 (1977); M. Kuroboshi, M. Tanaka, S. Kishimoto, H. Tanaka, S. Torii. Synlett. 69 (1999).
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Okude, Y.1
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80
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(b) Y. Okude, T. Hiyama, H. Nozaki. Tetrahedron Lett. 43, 3829 (1977); M. Kuroboshi, M. Tanaka, S. Kishimoto, H. Tanaka, S. Torii. Synlett. 69 (1999).
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Synlett
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Kuroboshi, M.1
Tanaka, M.2
Kishimoto, S.3
Tanaka, H.4
Torii, S.5
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81
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K. Takai, K. Nitta, O. Fujimura, K. Utimoto. J. Org. Chem. 54, 4732 (1989).
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Takai, K.1
Nitta, K.2
Fujimura, O.3
Utimoto, K.4
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82
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85038460182
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note
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3, (2) montmorillonite clay/i-PrOH, (3) PPTS/i-PrOH, and (4) amberlite 15/i-PrOH.
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