Efficient asymmetric synthesis of 1-alk-2-yne-1,4-diols

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8341-8344

  Diez, Roberto Sans ^a,b   Adger, Brian ^c   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF BURGOS   (Spain)

^c JOHNSON MATTHEY CATALYSTS   (United Kingdom)

Author keywords

1,4 diols; Asymmetric synthesis; Optically active compounds

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; METHYLEPHEDRINE; ZINC DERIVATIVE;

ARTICLE; DEPROTECTION REACTION; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037037959     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00985-7     Document Type: Article

References (27)

1. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
2. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
3. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
4. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
5. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
6. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
7. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
8. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
9. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
10. For selected examples of the use of optically active propargylicic alcohols in synthesis, see: (a) Midland M.M., Tramontano A. Tetrahedron Lett. 21:1980;3549 (b) Johnson W.S., Frei B., Gopalan A.S. J. Org. Chem. 46:1981;1512 (c) Midland M.M., Nguyen N.H. J. Org. Chem. 46:1981;4107 (d) Nicolaou K.C., Webber S.E. J. Am. Chem. Soc. 106:1984;5734 (e) Corey E.J., Niimura K., Konishi Y., Hashimoto S., Hamada Y. Tetrahedron Lett. 27:1986;2199 (f) Wender P.A., Ihle N.C., Correia C.R.D. J. Am. Chem. Soc. 110:1988;5904 (g) Trost B.M., Hipskind P.A., Chung J.Y.L., Chan C. Angew. Chem., Int. Ed. Engl. 28:1989;1502 (h) Marshall J.A., Wang X.J. J. Org. Chem. 57:1992;1242 (i) Roush W.R., Sciotti R.J. J. Am. Chem. Soc. 116:1994;6457 (j) Myers A.G., Zheng B. J. Am. Chem. Soc. 118:1996;4492.
11. For recent reports, see: (a) Gaul C., Seebach D. Helv. Chim. Acta. 85:2002;772 (b) Burk M.J., Martinez J.P., Feaster J.E., Cosford N. Tetrahedron. 50:1994;4399 (c) Amador M., Ariza X., Garcia J., Ortiz J. Tetrahedron Lett. 43:2002;2691 The last citation describes work carried out independently similar to that described in this manuscript. The appearance of such results prompts us to disclose our own work in the area which is the subject of a patent with Synetix.
12. For recent reports, see: (a) Gaul C., Seebach D. Helv. Chim. Acta. 85:2002;772 (b) Burk M.J., Martinez J.P., Feaster J.E., Cosford N. Tetrahedron. 50:1994;4399 (c) Amador M., Ariza X., Garcia J., Ortiz J. Tetrahedron Lett. 43:2002;2691 The last citation describes work carried out independently similar to that described in this manuscript. The appearance of such results prompts us to disclose our own work in the area which is the subject of a patent with Synetix.
13. For recent reports, see: (a) Gaul C., Seebach D. Helv. Chim. Acta. 85:2002;772 (b) Burk M.J., Martinez J.P., Feaster J.E., Cosford N. Tetrahedron. 50:1994;4399 (c) Amador M., Ariza X., Garcia J., Ortiz J. Tetrahedron Lett. 43:2002;2691 The last citation describes work carried out independently similar to that described in this manuscript. The appearance of such results prompts us to disclose our own work in the area which is the subject of a patent with Synetix.
14. (a) Frantz D.E., Fässler R., Carreira E.M. J. Am. Chem. Soc. 122:2000;1806
15. (b) Boyall D., López F., Sasaki H., Frantz D., Carreira E.M. Org. Lett. 2:2000;4233
16. (c) Sasaki H., Boyall D., Carreira E.M. Helv. Chim. Acta. 84:2001;964
17. (d) Anand N.K., Carreira E.M. J. Am. Chem. Soc. 123:2001;9687.
18. (a) Frantz D.E., Fässler R., Tomooka C.S., Carreira E.M. Acct. Chem. Res. 33:2000;373
19. (b) Frantz D.E., Fässler R., Carreira E.M. J. Am. Chem. Soc. 121:1999;11245
20. (c) Faessler R., Frantz D.E., Oetiker J., Carreira E.M. Angew. Chem. Int. Ed. 41:2002;3054.
21. For applications, see: (a) Bode J.W., Carreira E.M. J. Am. Chem. Soc. 123:2001;3611 (b) Bode J.W., Carreira E.M. J. Org. Chem. 66:2001;6410.
22. For applications, see: (a) Bode J.W., Carreira E.M. J. Am. Chem. Soc. 123:2001;3611 (b) Bode J.W., Carreira E.M. J. Org. Chem. 66:2001;6410.
23. Our work on the direct addition of acetylides to aldehydes, originates from our interest in discovering and developing reactions that may be conducted with readily available starting materials, see: (a) Carreira E.M., Lee W.L., Singer R.A. J. Am. Chem. Soc. 117:1995;3649 (b) Gauthier D.R. Jr., Carreira E.M. Angew. Chem. 108:1996;2521 (c) Gauthier D.R. Jr., Carreira E.M. Angew. Chem., Int. Ed. Engl. 35:1996;2363 (d) Bode J.W., Gauthier D.R. Jr., Carreira E.M. Chem. Comm. 2001;2560 (e) Fischer C., Carreira E.M. Org. Lett. 3:2001;4319.
24. Our work on the direct addition of acetylides to aldehydes, originates from our interest in discovering and developing reactions that may be conducted with readily available starting materials, see: (a) Carreira E.M., Lee W.L., Singer R.A. J. Am. Chem. Soc. 117:1995;3649 (b) Gauthier D.R. Jr., Carreira E.M. Angew. Chem. 108:1996;2521 (c) Gauthier D.R. Jr., Carreira E.M. Angew. Chem., Int. Ed. Engl. 35:1996;2363 (d) Bode J.W., Gauthier D.R. Jr., Carreira E.M. Chem. Comm. 2001;2560 (e) Fischer C., Carreira E.M. Org. Lett. 3:2001;4319.
25. Our work on the direct addition of acetylides to aldehydes, originates from our interest in discovering and developing reactions that may be conducted with readily available starting materials, see: (a) Carreira E.M., Lee W.L., Singer R.A. J. Am. Chem. Soc. 117:1995;3649 (b) Gauthier D.R. Jr., Carreira E.M. Angew. Chem. 108:1996;2521 (c) Gauthier D.R. Jr., Carreira E.M. Angew. Chem., Int. Ed. Engl. 35:1996;2363 (d) Bode J.W., Gauthier D.R. Jr., Carreira E.M. Chem. Comm. 2001;2560 (e) Fischer C., Carreira E.M. Org. Lett. 3:2001;4319.
26. Our work on the direct addition of acetylides to aldehydes, originates from our interest in discovering and developing reactions that may be conducted with readily available starting materials, see: (a) Carreira E.M., Lee W.L., Singer R.A. J. Am. Chem. Soc. 117:1995;3649 (b) Gauthier D.R. Jr., Carreira E.M. Angew. Chem. 108:1996;2521 (c) Gauthier D.R. Jr., Carreira E.M. Angew. Chem., Int. Ed. Engl. 35:1996;2363 (d) Bode J.W., Gauthier D.R. Jr., Carreira E.M. Chem. Comm. 2001;2560 (e) Fischer C., Carreira E.M. Org. Lett. 3:2001;4319.
27. Our work on the direct addition of acetylides to aldehydes, originates from our interest in discovering and developing reactions that may be conducted with readily available starting materials, see: (a) Carreira E.M., Lee W.L., Singer R.A. J. Am. Chem. Soc. 117:1995;3649 (b) Gauthier D.R. Jr., Carreira E.M. Angew. Chem. 108:1996;2521 (c) Gauthier D.R. Jr., Carreira E.M. Angew. Chem., Int. Ed. Engl. 35:1996;2363 (d) Bode J.W., Gauthier D.R. Jr., Carreira E.M. Chem. Comm. 2001;2560 (e) Fischer C., Carreira E.M. Org. Lett. 3:2001;4319.