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For other catalytic direct aldol reactions, see: (k) Mahrwald R., Gundogan B. J. Am. Chem. Soc. 120:1998;413 (l) Mascarenhas C.M., Duffey M.O., Liu S.-Y., Morken J.P. Org. Lett. 1:1999;1427 (m) Loh T.-P., Wei L.-L., Feng L.-C. Synlett. 1999;1059 (n) Taylor S.J., Duffey M.O., Morken J.P. J. Am. Chem. Soc. 122:2000;4528 (o) Evans D.A., Tedrow J.S., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 124:2002;392.
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For other catalytic direct aldol reactions, see: (k) Mahrwald R., Gundogan B. J. Am. Chem. Soc. 120:1998;413 (l) Mascarenhas C.M., Duffey M.O., Liu S.-Y., Morken J.P. Org. Lett. 1:1999;1427 (m) Loh T.-P., Wei L.-L., Feng L.-C. Synlett. 1999;1059 (n) Taylor S.J., Duffey M.O., Morken J.P. J. Am. Chem. Soc. 122:2000;4528 (o) Evans D.A., Tedrow J.S., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 124:2002;392.
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For other catalytic direct aldol reactions, see: (k) Mahrwald R., Gundogan B. J. Am. Chem. Soc. 120:1998;413 (l) Mascarenhas C.M., Duffey M.O., Liu S.-Y., Morken J.P. Org. Lett. 1:1999;1427 (m) Loh T.-P., Wei L.-L., Feng L.-C. Synlett. 1999;1059 (n) Taylor S.J., Duffey M.O., Morken J.P. J. Am. Chem. Soc. 122:2000;4528 (o) Evans D.A., Tedrow J.S., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 124:2002;392.
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For other catalytic direct aldol reactions, see: (k) Mahrwald R., Gundogan B. J. Am. Chem. Soc. 120:1998;413 (l) Mascarenhas C.M., Duffey M.O., Liu S.-Y., Morken J.P. Org. Lett. 1:1999;1427 (m) Loh T.-P., Wei L.-L., Feng L.-C. Synlett. 1999;1059 (n) Taylor S.J., Duffey M.O., Morken J.P. J. Am. Chem. Soc. 122:2000;4528 (o) Evans D.A., Tedrow J.S., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 124:2002;392.
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For other catalytic direct aldol reactions, see: (k) Mahrwald R., Gundogan B. J. Am. Chem. Soc. 120:1998;413 (l) Mascarenhas C.M., Duffey M.O., Liu S.-Y., Morken J.P. Org. Lett. 1:1999;1427 (m) Loh T.-P., Wei L.-L., Feng L.-C. Synlett. 1999;1059 (n) Taylor S.J., Duffey M.O., Morken J.P. J. Am. Chem. Soc. 122:2000;4528 (o) Evans D.A., Tedrow J.S., Shaw J.T., Downey C.W. J. Am. Chem. Soc. 124:2002;392.
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For recent examples of proline-catalyzed reactions, see: (a) Hanessian S., Pham V. Org. Lett. 2:2000;2975 (b) Bui T., Barbas C.F. III. Tetrahedron Lett. 41:2000;6951 © List B. J. Am. Chem. Soc. 122:2000;9336 (d) Notz W., Sakthivel K., Bui T., Zhong G., Barbas C.F. III. Tetrahedron Lett. 42:2001;199 (e) Benaglia M., Celentano G., Cozzi F. Adv. Synth. Catal. 343:2001;171 (f) List B., Pojarliev P., Martin H.J. Org. Lett. 3:2001;2423 (g) List B., Castello C. Synlett. 2001;1687 (h) Córdova A., Notz W., Barbas C.F. III. J. Org. Chem. 67:2002;301 (i) Enders D., Seki A. Synlett. 2002;26 (j) List B., Pojarliev P., Biller W.T., Martin. J. Am. Chem. Soc. 124:2002;827 (k) Córdova A., Notz W., Zhong G., Betancort J.M., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1842 (l) Córdova A., Watanabe S., Tanaka F., Notz W., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1866.
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For recent examples of proline-catalyzed reactions, see: (a) Hanessian S., Pham V. Org. Lett. 2:2000;2975 (b) Bui T., Barbas C.F. III. Tetrahedron Lett. 41:2000;6951 © List B. J. Am. Chem. Soc. 122:2000;9336 (d) Notz W., Sakthivel K., Bui T., Zhong G., Barbas C.F. III. Tetrahedron Lett. 42:2001;199 (e) Benaglia M., Celentano G., Cozzi F. Adv. Synth. Catal. 343:2001;171 (f) List B., Pojarliev P., Martin H.J. Org. Lett. 3:2001;2423 (g) List B., Castello C. Synlett. 2001;1687 (h) Córdova A., Notz W., Barbas C.F. III. J. Org. Chem. 67:2002;301 (i) Enders D., Seki A. Synlett. 2002;26 (j) List B., Pojarliev P., Biller W.T., Martin. J. Am. Chem. Soc. 124:2002;827 (k) Córdova A., Notz W., Zhong G., Betancort J.M., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1842 (l) Córdova A., Watanabe S., Tanaka F., Notz W., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1866.
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For recent examples of proline-catalyzed reactions, see: (a) Hanessian S., Pham V. Org. Lett. 2:2000;2975 (b) Bui T., Barbas C.F. III. Tetrahedron Lett. 41:2000;6951 © List B. J. Am. Chem. Soc. 122:2000;9336 (d) Notz W., Sakthivel K., Bui T., Zhong G., Barbas C.F. III. Tetrahedron Lett. 42:2001;199 (e) Benaglia M., Celentano G., Cozzi F. Adv. Synth. Catal. 343:2001;171 (f) List B., Pojarliev P., Martin H.J. Org. Lett. 3:2001;2423 (g) List B., Castello C. Synlett. 2001;1687 (h) Córdova A., Notz W., Barbas C.F. III. J. Org. Chem. 67:2002;301 (i) Enders D., Seki A. Synlett. 2002;26 (j) List B., Pojarliev P., Biller W.T., Martin. J. Am. Chem. Soc. 124:2002;827 (k) Córdova A., Notz W., Zhong G., Betancort J.M., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1842 (l) Córdova A., Watanabe S., Tanaka F., Notz W., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1866.
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For recent examples of proline-catalyzed reactions, see: (a) Hanessian S., Pham V. Org. Lett. 2:2000;2975 (b) Bui T., Barbas C.F. III. Tetrahedron Lett. 41:2000;6951 © List B. J. Am. Chem. Soc. 122:2000;9336 (d) Notz W., Sakthivel K., Bui T., Zhong G., Barbas C.F. III. Tetrahedron Lett. 42:2001;199 (e) Benaglia M., Celentano G., Cozzi F. Adv. Synth. Catal. 343:2001;171 (f) List B., Pojarliev P., Martin H.J. Org. Lett. 3:2001;2423 (g) List B., Castello C. Synlett. 2001;1687 (h) Córdova A., Notz W., Barbas C.F. III. J. Org. Chem. 67:2002;301 (i) Enders D., Seki A. Synlett. 2002;26 (j) List B., Pojarliev P., Biller W.T., Martin. J. Am. Chem. Soc. 124:2002;827 (k) Córdova A., Notz W., Zhong G., Betancort J.M., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1842 (l) Córdova A., Watanabe S., Tanaka F., Notz W., Barbas C.F. III. J. Am. Chem. Soc. 124:2002;1866.
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In the meanwhile, diamine 4-(1S)-camphorsulfonic acid catalayst was reported to promote the direct aldol reaction and the asymmetric three-component Mannich-type reaction by Barbas, III, see Refs. 7d,8d. Diamine 4 alone tested for the Mannich-type reaction by List, see Ref. 8j and: supporting information of Ref. 8c. Diamine 4 alone tested for the direct asymmetric Michael reaction and the asymmetric Robinson annulation reaction by Barbas, III, see Ref. 8b and: (a) Betancort J.M., Barbas C.F. III. Org. Lett. 3:2001;3737 (b) Betancort J.M., Sakthivel K., Thayumanavan R., Barbas C.F. III. Tetrahedron Lett. 42:2001;4441.
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In the meanwhile, diamine 4-(1S)-camphorsulfonic acid catalayst was reported to promote the direct aldol reaction and the asymmetric three-component Mannich-type reaction by Barbas, III, see Refs. 7d,8d. Diamine 4 alone tested for the Mannich-type reaction by List, see Ref. 8j and: supporting information of Ref. 8c. Diamine 4 alone tested for the direct asymmetric Michael reaction and the asymmetric Robinson annulation reaction by Barbas, III, see Ref. 8b and: (a) Betancort J.M., Barbas C.F. III. Org. Lett. 3:2001;3737 (b) Betancort J.M., Sakthivel K., Thayumanavan R., Barbas C.F. III. Tetrahedron Lett. 42:2001;4441.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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0000166505
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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0001013917
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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These diamines were prepared by the methods previously described, see: (a) Saito I., Kikugawa Y., Yamada S. Chem. Pharm. Bull. 18:1970;1731 (b) Asami M., Ohno H., Kobayashi S., Mukaiyama T. Bull. Chem. Soc. Jpn. 51:1978;1869 © Mukaiyama T., Soai K., Sato T., Shimizu H., Suzuki K. J. Am. Chem. Soc. 101:1979;1455 (d) Mukaiyama T. Tetrahedron. 37:1981;4111 (e) Mukaiyama T., Iwasawa N., Stevens R.W., Haga T. Tetrahedron. 40:1984;1381 (f) Mukaiyama T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (g) Hendrie T., Kobayashi S., Sano T. Tetrahedron. 46:1984;4653 (h) Kobayashi S., Uchiro H., Fujishita Y., Shiina I., Mukaiyama T.J. J. Am. Chem. Soc. 113:1991;4247 (i) Yuste F., Ortiz B., Carrasco A., Peralta M., Quintero L., Schez-Obregon R., Walls F., Ruano J.L.G. Tetrahedron: Asymmetry. 11:2000;3079.
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Crystallographic data (excluding structure factors) for the X-ray crystal structure analysis reported in this paper have been deposited with Cambridge Crystallographic Data Center (CCDC) as supplementary publication no. CCDC-184706. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk)
-
Crystallographic data (excluding structure factors) for the X-ray crystal structure analysis reported in this paper have been deposited with Cambridge Crystallographic Data Center (CCDC) as supplementary publication no. CCDC-184706. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk).
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