Crystal engineering for absolute asymmetric synthesis through the use of meta substituted aryl groups

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3135-3138

  Wu, Lian Chung ^a   Cheer, Clair J ^a   Olovsson, Gunnar ^b   Scheffer, John R ^b   Trotter, James ^a,b   Wang, Sue Lein ^c   Liao, Fen Ling ^c  

^a University of Rhode Island   (United States)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^c NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; IRRADIATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030980062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00615-1     Document Type: Article

References (18)

1. The first absolute asymmetric synthesis was reported by Penzien, K.; Schmidt, G.M.J. Angew. Chem., Int. Ed. Engl. 1969, 8, 608.
2. (a) Vaida, M.; Popovitz-Biro, R.; Leiserowitz, L.; Lahav, M. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 6;
3. (b) Caswell, L.; Garcia-Garibay, M.A.; Scheffer, J.R.; Trotter, J. J. Chem. Ed. 1993, 70, 785.
4. Jacques, J.; Collet, A.; Wilen, S.H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981.
5. Curtin, D.Y.; Paul, I.C. Chem. Rev. 1981, 81, 525.
6. Taylor, E.C.; Paudler, W.W. Tetrahedron Lett. 1960, 1.
7. Kaneko, C.; Katagiri, N.; Sato, M.; Muto, M.; Sakamoto, T.; Saikawa, S.; Naito, T.; Saito, A. J. Chem. Soc., Perkin Trans. 1 1986, 1283 and references cited therein.
8. Sato, M.; Katagiri, N.; Muto, M.; Haneda, T.; Kaneko, C. Tetrahedron Lett. 1986, 27, 6091.
9. Toda, F.; Tanaka, K. Tetrahedron Lett. 1988, 29, 4299.
10. (a) Ochiai, E. J. Org. Chem. 1953, 18, 534;
11. (b) Shone, R.L.; Coker, V.M.; Moormann, A.E. J. Heterocyclic Chem. 1975, 12, 389.
12. 1a: a = 8.203(8), b = 25.99(3), c = 4.996(5) Å; Z = 4, R = 4.4%. 1b: a = 8.1502(6), b = 25.692(2), c = 5.2180(7) Å; Z = 4, R = 3.5%. 1c: a = 8.118(1), b = 26.359(2), c = 5.280(2) Å; Z = 4, R = 2.8%. 1d: a = 8.215(1), b = 26.2972(9), c = 5.057(3) Å; Z = 4, R = 3.4%. 1e: a = 5.767(5), b = 21.189(12), c = 8.577(7) Å; β= 101.11°; Z = 4, R = 5.7%. 1f: a = 11.327(1), b = 12.552(1), c = 8.5003(6) Å; α = 101.90(3), β = 110.81(6), γ = 80.04(0)°; Z = 4, R = 4.5%. 1g: a = 11.2525(8), b = 12.763(1), c = 8.1126(8) Å; α = 108.39(7), β = 99.36(9), γ = 92.76(9)°; Z = 4, R = 3.8%. 1h: a = 6.071(2), b = 8.649(2), c = 13.970(4) Å; α = 87.46(2), β = 81.29(3), γ = 77.14(3)°; Z = 2, R = 5.3%. Full crystallographic details will be published separately.
13. Thermal cycloreversion of compounds of type 2 is known. See for example Sato, E.; Ikeda, Y.; Kanoaka, Y. Heterocycles 1987, 26, 1611.
14. Leibovitch, M.; Olovsson, G.; Sundarababu, G.; Ramamurthy, V.; Scheffer, J.R.; Trotter, J. J. Am. Chem. Soc. 1996, 118, 1219.
15. (a) Garcia-Garibay, M.; Scheffer, J.R.; Trotter, J.; Wireko, F. J. Am. Chem. Soc. 1989, 111, 4985;
16. (b) Fu, T.Y.; Liu, Z.; Scheffer, J.R.; Trotter, J. J. Am. Chem. Soc. 1993, 115, 12, 202.
17. Weiss, R.G.; Ramamurthy, V.; Hammond, G.S. Acc. Chem. Res. 1993, 26, 530.
18. Hashizume, D.; Kogo, H.; Sekine, A.; Ohashi, Y.; Miyamoto, H.; Toda, F. J. Chem. Soc., Perkin Trans. 2 1996, 61.