Novel and efficient method for esterification, amidation between carboxylic acids and equimolar amounts of alcohols, and amines utilizing Me2NSO2Cl and N,N-dimethylamines; Its application to the synthesis of coumaperine, a natural chemopreventive dieneamide

Tetrahedron

Volumn 59, Issue 28, 2003, Pages 5337-5345

  Wakasugi, Kazunori ^a   Nakamura, Atsushi ^a   Iida, Akira ^a   Nishii, Yoshinori ^a   Nakatani, Nobuji ^b   Fukushima, Shoji ^b   Tanabe, Yoo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Amidation; Coumaperine; Esterification; Sulfamoyl chloride; Tertiary amine

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; CARBONYL DERIVATIVE; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE; COUMAPERINE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL REACTION; CHEMOPROPHYLAXIS; CHEMOSENSITIVITY; DRUG SYNTHESIS; ESTERIFICATION; PRIORITY JOURNAL;

EID: 0042709497     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00734-8     Document Type: Article

References (68)

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16. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
17. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
18. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
19. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
20. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
21. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
22. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
23. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
24. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
25. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
26. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
27. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
28. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
29. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
30. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
31. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
32. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
33. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
34. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
35. For selected examples: (a) Brewster J.H., Ciotti C.J. Jr. J. Am. Chem. Soc. 77:1955;6214 (b) Parish R.C., Stock L.M. J. Org. Chem. 30:1965;927 (c) Hendrickson J.B., Schwartzman S.M. Tetrahedron Lett. 16:1975;277 (d) Rehn D., Ugi I. J. Chem. Res. (S). 1977;119 (e) Liu H.-J., Chan W.H., Lee S.P. Tetrahedron Lett. 19:1978;4461 (f) Venkataraman K., Wagle D.R. Tetrahedron Lett. 1979;3073 (g) Candrasekaran S., Turner J.V. Synth. Commun. 12:1982;727 (h) Mukaiyama T., Ichikawa J., Asami M. Chem. Lett. 1983;683 (i) Ramaiah M. J. Org. Chem. 50:1985;4991 (j) Shono T., Ishige O., Uyama H., Kashimura S. J. Org. Chem. 51:1986;546 (k) Otera J., Dan-oh N., Nozaki H. J. Org. Chem. 56:1991;5307 (l) Folmer J.J., Weinreb S.M. Tetrahedron Lett. 34:1993;2737 (m) Takeda K., Akiyama H., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., Harigaya Y. Synthesis. 1994;1063 (n) Shiina I., Miyoshi S., Miyashita M., Mukaiyama T. Chem. Lett. 1994;515 (o) Zacharie B., Connolly T.P., Penney C.L. J. Org. Chem. 60:1995;7072 (p) Vedejs E., Daugulis O. J. Org. Chem. 61:1996;5702 (q) Hosangadi B.D., Dave R.H. Tetrahedron Lett. 37:1996;6375 (r) Wright S.W., Hageman D.L., McClure L.D. Tetrahedron Lett. 38:1997;7345 (s) Thierry J., Yue C., Potier P. Tetrahedron Lett. 39:1998;1557 (t) Kunishima M., Morita J., Kawachi C., Iwasaki F., Terao K., Tani S. Synlett. 1999;1255.
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