Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels-Alder reactions

Tetrahedron

Volumn 59, Issue 52, 2003, Pages 10509-10523

  Furuno, Hiroshi ^a   Hayano, Tetsuji ^a   Kambara, Takeshi ^b   Sugimoto, Yuichi ^a   Hanamoto, Takeshi ^a,c   Tanaka, Yumiko ^a   Jin, Yong Zhi ^a   Kagawa, Takumi ^b   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOSOH CORPORATION   (Japan)

^c SAGA UNIVERSITY   (Japan)

Author keywords

Asymmetric amplification; Chiral Lewis acid catalyst; Chiral rare earth metal complex; Enantioselective hetero Diels Alder reaction; Homogeneous catalysis

Indexed keywords

ALDEHYDE DERIVATIVE; ALKADIENE; LANTHANIDE; LIGAND; ORGANOPHOSPHATE; SCANDIUM; YTTERBIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; ROOM TEMPERATURE;

BETULACEAE;

EID: 0347419459     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.06.011     Document Type: Article

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49. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
50. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
51. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
52. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
53. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
54. For some recent reports of the highly enantioselective hetero-Diels-Alder reaction of aldehydes with the diene 6, see: (a) Yamashita Y., Saito S., Ishitani H., Kobayashi S. J. Am. Chem. Soc. 125:2003;3793-3798 (b) Yuan Y., Long J., Sun J., Ding K. Chem. Eur. J. 8:2002;5033-5042 (c) Kii S., Hashimoto T., Maruoka K. Synlett. 2002;931-932 (d) Wang B., Feng X., Huang Y., Liu H., Cui X., Jiang Y. J. Org. Chem. 67:2002;2175-2182 (e) Du H., Long J., Hu J., Li X., Ding K. Org. Lett. 4:2002;4349-4352 (f) Doyle M.P., Phillips I.M., Ju W. J. Am. Chem. Soc. 123:2001;5366-5367 (g) Aikawa K., Irie R., Katsuki T. Tetrahedron. 57:2001;845-851 (h) Kezuka S., Mita T., Ohtsuki N., Ikeno T., Yamada T. Bull. Chem. Soc. Jpn. 74:2001;1333-1342 (i) Bednarski M., Maring C., Danishefsky S. Tetrahedron Lett. 24:1983;3451-3454.
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