First catalytic asymmetric hydrophosphonylation of cyclic imines: Highly efficient enantioselective approach to a 4-thiazolidinylphosphonate via chiral titanium and lanthanoid catalysts

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9291-9292

  Gröger, Harald ^a   Saida, Yoshinobu ^b   Arai, Shigeru ^b   Martens, Jürgen ^a   Sasai, Hiroaki ^b   Shibasaki, Masakatsu ^b  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0039150859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82944-9     Document Type: Article

References (14)

1. 1. a) K. J. M. Andrews, Eur. Pat. 33919, 1981, Hoffmann-La Roche; Chem. Abstr. 1982, 96, 52498r;
2. b) K. Drauz, H. G. Koban, J. Martens, W. Schwarze, Liebigs Ann. Chem. 1985, 448-452;
3. c) K. Drauz, H. G. Koban, J. Martens, W. Schwarze, US Pat. 4524211, 1985, Degussa AG; Chem. Abstr. 1984,101, 211458x.
4. 2. Titanium L-dipt-catalyst was prepared in situ; whereas the corresponding titanium (R)-BINOL-and (R,R)-TADDOL-catalysts were isolated prior to use according to the literature: a) Titanium-BINOL-complex: J. T. Wang, X. Fan, X. Feng, Y.-M. Qian, Synthesis, 1989, 291-292;
5. b) Titanium-TADDOL-complex: D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta 1992, 75, 2171-2209.
6. 3. a) T. Yokomatsu, T. Yamagishi, S. Shibuya, Tetrahedron: Asymmetry 1993, 4, 1779-1782;
7. b) For a review see: R. O. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807-832.
8. 4. H. Sasai, S. Arai, Y. Tahara, M. Shibasaki, J. Org. Chem. 1995, 60, 6656-6657. All the lanthanoid catalysts were prepared from corresponding lanthanoid isopropoxide, purchased from Kojundo Chemical Laboratory Co. Ltd., Saitama, Japan.
9. 5. a) H. Sasai, Y. M. A. Yamada, T. Suzuki, M. Shibasaki, Tetrahedron 1994, 50, 12313-12318;
10. b) H. Sasai, T. Arai, Y. Satow, K. N. Houk, M. Shibasaki, J. Am. Chem. Soc. 1995, 117, 6194-6198;
11. c) M. Shibasaki, H. Sasai, Pure Appl. Chem. 1996, 68, 523-530;
12. d) T. Arai, M. Bougauchi, H. Sasai, M. Shibasaki, J. Org. Chem. 1996, 61, 2926-2927.
13. 6. The absolute configuration of the major enantiomer was determined based on correlation of the sign of optical rotation of the hydrolyzed product of 2 with those of the authentic (R)-and (S)-enantiomers, described in: I. Hoppe, U. Schöllkopf, M. Nieger, K. Egert, Angew. Chem. 1985, 97, 1066-1067; Angew. Chem. Int. Ed. Engl. 1985, 24, 1036-1037.
14. 6. The absolute configuration of the major enantiomer was determined based on correlation of the sign of optical rotation of the hydrolyzed product of 2 with those of the authentic (R)-and (S)-enantiomers, described in: I. Hoppe, U. Schöllkopf, M. Nieger, K. Egert, Angew. Chem. 1985, 97, 1066-1067; Angew. Chem. Int. Ed. Engl. 1985, 24, 1036-1037.