Coupling reaction of 4-cyclopentene-1,3-diol monoacetate and lithium alkenylborates and its application to chiral synthesis of prostaglandin intermediates

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 601-604

  Usmani, Shahid B ^a   Takahisa, Eisuke ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; LITHIUM DERIVATIVE; NICKEL; PROSTAGLANDIN DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032509940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10655-4     Document Type: Article

References (21)

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7. (f) Sugai, T.; Mori, K. Synthesis 1988, 19-22.
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12. 4. Deardorff, D. R.; Myles, D. C. In Organic Syntheses; Freeman, J. P., Ed.; Wiley: New York, 1993; Collect. Vol. 8, pp 13-16.
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16. 7. Dixon, A. J.; Taylor, R. J. K.; Newton, R. F. J. Chem. Soc., Perkin I 1981, 1407-1410.
17. 8. (a) Chapleo, C. B.; Finch, M. A. W.; Lee, T. V.; Roberts, S. M.; Newton, R. F. J. Chem. Soc., Perkin I 1980, 2084-2087.
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19. - with acetate 1 to produce i; (3) ligand exchange of i with borate 3 and reductive elimination to furnish 4 and Ni(0) before changing into the thermodynamically stable π-allyl intermediate(s). Electron donating t-BuCN conceivably accelerates the above step(s). (formula presented)
20. - (X = Cl, Br, I): see, Negishi, E.; Takahashi, T.; Akiyoshi, K. J. Chem. Soc., Chem. Commun. 1986, 1338-1339.
21. 3) data of 4a: δ0.90 (t, J = 7 Hz, 3 H), 1.1-1.5 (m, 7 H), 1.78-1.97 (m, 4 H), 3.47 (q, J = 7 Hz, 1 H), 4.85-4.91 (m, 1 H), 5.22 (ddt, J = 8, 15, 1 Hz, 1 H), 5.44 (dt, J = 15, 7 Hz, 1 H), 5.82 (br s, 2 H); 4b: δ0.91 (t, J = 7 H, 3 H), 1.2-1.5 (m, 6 H), 1.6 (br s, 1 H), 1.85 (ddd, J = 5, 7, 14 Hz, 1 H), 2.01 (ddd, J = 2.5, 8, 14 Hz, 1 H), 2.08 (dq, J = 1, 7 Hz, 2 H), 3.78-3.89 (m, 1 H), 4.86-4.94 (m, 1 H), 5.09 (tt, J = 1.5, 10 Hz, 1 H), 5.38 (ddt, J = 1, 10, 7 Hz, 1 H), 5.80 (dd, J = 2, 5.5 Hz, 1 H), 5.87 (dt, J = 2, 5.5 Hz, 1 H); 9: δ - 0.003 (s, 3 H), 0.02 (s, 3 H), 0.87 (s, 12 H), 1.18-1.56 (m, 8 H), 1.6 (br s, 1 H), 1.82-2.04 (m, 2 H), 3.49 (q, J = 7 Hz, 1 H), 3.99 (q, J = 6 Hz, 1 H), 4.84-4.94 (m, 1 H), 5.35 (dd, J = 7, 15 Hz, 1 H), 5.42 (dd, J = 6, 15 Hz, 1 H), 5.86 (s, 2 H); 11: δ -0.01 (s, 3 H), 0.01 (s, 3 H), 0.86 (s, 12 H), 1.20-1.56 (m, 8 H), 1.76 (br s, 1 H), 1.82-2.02 (m, 2 H), 3.46 (q, J = 6 Hz, 1 H), 3.99 (q, J = 7 Hz, 1 H), 4.83-4.92 (m, 1 H), 5.34 (dd, J = 7, 16 Hz, 1 H), 5.41 (dd, J = 6, 16 Hz, 1 H), 5.80-5.89 (m, 2 H).