The mechanism of configuration retention in the substitution reaction of C4-tosyloxyproline with lithium diarylcuprate

Heterocycles

Volumn 42, Issue 2, 1996, Pages 489-492

  Hashimoto, Kimiko ^a,b   Shima, Yukio ^a   Shirahama, Haruhisa ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000609226     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s72     Document Type: Article

References (9)

1. G. M. Coppola and H. F. Schuster, 'Asymmetric Synthesis, Construction of Chiral Molecules Using Amino Acids', John-Wiley & Sons, 1987, Chap. 8.4.
2. J. K. Thottathil and J. L. Moniot, Tetrahedron Lett., 1986, 27, 151.
3. K. Hashimoto and H. Shirahama, Tetrahedron Lett., 1991, 32, 2625.
4. Unpublished results.
5. Participation of double bond in the substitution reaction of tosylate with organocuprate is reported : G. H. Posner and J.-S. Ting, Tetrahedron Lett., 1974, 683.
6. (a) The cis-isomer (14) was prepared according to the following papers: M. M. Bowers-Nemia and M. M. Joullié, Heterocycles, 1983, 20, 817. A. A. Patchett and B. Witkop, J. Am. Chem. Soc., 1957, 79, 185.
7. (a) The cis-isomer (14) was prepared according to the following papers: M. M. Bowers-Nemia and M. M. Joullié, Heterocycles, 1983, 20, 817. A. A. Patchett and B. Witkop, J. Am. Chem. Soc., 1957, 79, 185.
8. (b) The trans-isomer (1) was prepared according to the reference 2.
9. 3) for 12: δ (ppm) 1.47(9H, s), 2.03(1H, m), 2.17(1H, dt, J=12.5, 8.0Hz), 3.35-3.54(2H, m), 3.65-3.83(3H, m), 4.20(1H, m), 4.34(1H, brs), 7.20-7.35(5H, m). 13: δ 1.49(9H, s), 1.67(1H, q, J=10.7Hz), 2.41(1H, dt, J=10.7, 5.3Hz), 3.20-3.30(2H, m), 3.68(1H, ddd, J=1.3, 8.0, 12.0Hz), 3.76(1H, t, J=12.0Hz), 3.99(1H, m), 4.09(1H, dddd, J=5.3, 8.0, 10.7, 12.0Hz), 5.29(1H, dd, J=1.3, 12.0Hz), 7.21-7.36(5H, m).