One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole

Advanced Synthesis and Catalysis

Volumn 342, Issue 7, 2000, Pages 654-658

  Christoffers, Jens ^a   Rößler, Ulrich ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Alkylations; Chirality; Hydroxy acids; Protecting groups; Synthetic methods

Indexed keywords

EID: 0346043273     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3897(200009)342:7<654::aid-prac654>3.3.co;2-q     Document Type: Article

References (28)

1. a) J. Christoffers, A. Mann, Angew. Chem., in press;
2. b) J. Christoffers, U. Rößler, T. Werner, Eur. J. Org. Chem. 2000, 701;
3. c) J. Christoffers, J. Prakt. Chem. 1999, 341, 495;
4. d) J. Christoffers, A. Mann, Eur. J. Org. Chem. 1999, 1475;
5. e) J. Christoffers, A. Mann, J. Pickardt, Tetrahedron 1999, 55, 5377
6. a) J. Christoffers, Helv. Chim. Acta 1998, 81, 845;
7. b) J. Christoffers, Liebigs Ann./Recueil 1997, 1353
8. J. Christoffers, U. Rößler, Tetrahedron: Asymmetry 1999, 10, 1207
9. a) J. Mulzer, A. Angermann, Tetrahedron Lett. 1983, 24, 2843;
10. b) L. Colombo, M. Di Giacomo, G. Brusotti, G. Delogu, Tetrahedron Lett. 1994, 35, 2063;
11. c) K.-Y. Ko, E. L. Eliel, J. Org. Chem. 1986, 51, 5353
12. a) N. Iranpoor, I. M. Baltork, Tetrahedron Lett. 1990, 31, 735;
13. b) Y. Masaki, T. Miura, M. Ochiai, Bull. Chem. Soc. Jpn. 1996, 69, 195;
14. c) J. Otera, Y. Niibo, H. Nozaki, Tetrahedron 1991, 47, 7625
15. P. Varelis, B. L. Johnson, Austr. J. Chem. 1995, 48, 1775
16. a) K. Takai, C. H. Heathcock, J. Org. Chem. 1985, 50, 3247;
17. b) H. G. Aurich, F. Biesemeier, M. Boutahar, Chem. Ber. 1991, 124, 2329;
18. c) H. G. Aurich, F. Biesemeier, Synthesis 1995, 1171;
19. d) A. Solladie-Cavallo, F. Bonne, Tetrahedron: Asymmetry 1996, 7, 171;
20. e) F. Hammerschmidt, Monatsh. Chem. 1991, 122, 389
21. F. Cramer, K. Pawelzik, H. J. Baldauf, Chem. Ber. 1958, 91, 1049
22. a) U. Widmer, Synthesis 1987, 568;
23. b) H.-P. Wessel, T. Iversen, D. R. Bundle, J. Chem. Soc., Perkin Trans. 1 1985, 2247
24. P. Eckenberg, U. Groth, T. Huhn, N. Richter, C. Schmeck, Tetrahedron 1993, 49, 1619
25. a) Y. Ito, Y. Kobayashi, T. Kawabata, M. Takase, S. Terashima, Tetrahedron 1989, 45, 5767;
26. b) P. Van de Weghe, C. Bied, J. Collin, J. Marcalo, I. Santos, J. Organomet. Chem. 1994, 475, 121
27. G. E. Keck, M. B. Andrus, D. R. Romer, J. Org. Chem. 1991, 56, 417
28. J. Christoffers, U. Rößler, Tetrahedron: Asymmetry 1998, 9, 2349