Synthesis of optically active α-methyl β-hydroperoxy esters by diastereoselective singlet oxygen ene reaction and horseradish peroxidase catalyzed kinetic resolution

Monatshefte fur Chemie

Volumn 131, Issue 6, 2000, Pages 697-705

  Adam, Waldemar ^a   Saha Mo̊ller, Chantu R ^a   Weichold, Oliver ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Horseradish peroxidase; Kinetic resolution; Schenck ene reaction; Singlet oxygen; , Unsaturated hydroperoxy esters

Indexed keywords

EID: 0005177984     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007060070098     Document Type: Article

References (25)

1. Johnson RA, Sharpless KB (1993) In: Ojima I (ed) Catalytic Asymmetric Synthesis, VCH, Weinheim, p 103;
2. b) Murahashi SI, Komiya N (1998) Catal Today 41: 339
3. a) Adam W, Korb MN, Roschmann KJ, Saha-Möller CR (1998) J Org Chem 63: 3423;
4. b) Hamann HJ, Höft E, Chmielewski M, Maciejewski S (1993) Chirality 5: 338;
5. c) Hamann HJ, Höft E, Mostowicz D, Mishnev A, Urbańczyk-Lipkowska Z, Chmielewski M (1997) Tetrahedron 53: 185;
6. d) Shum WP, Saxton RJ, Zajacek JG (1997) US Patent 5, 663, 384
7. a) Baba N, Mimura M, Hiratake J, Uchida K, Oda J (1988) Agric Biol Chem 52: 2685;
8. b) Fu H, Kondo H, Ichikawa Y, Look GC, Wong CH (1992) J Org Chem 57: 7265
9. Adam W, Lazarus M, Saha-Möller CR, Weichold O, Hoch U, Häring D, Schreier P (1999) In: Faber K (ed) Advances in Biochemical Engineering/Biotechnology, vol 63. Springer, Heidelberg, p 73
10. von Auwers K (1923) Chem Ber 46
11. Buchta E, Burger K (1952) Justus Liebigs Ann Chem 576: 156
12. Johnstone RAW, Rose ME (1979) Pure Appl Chem 35: 2169
13. Kende AS, Toder BH (1982) J Org Chem 47: 163
14. Mukhopadhyay T, Seebach D (1982) Helv Chim Acta 65: 385
15. Adam W, Brünker HG, Sampath Kumar A, Peters EM, Peters K, Schneider U, von Schnering HG (1996) J Am Chem Soc 118: 1899
16. Adam W, Nestler B (1992) J Am Chem Soc 114: 6549
17. Chen CS, Fujimoto Y, Girdaukas G, Sih CJ (1982) J Am Chem Soc 104: 7294
18. Kazandjian RZ, Klibanov AM (1985) J Am Chem Soc 107: 5448
19. a) Adam W, Hoch U, Lazarus M, Saha-Möller CR, Schreier P (1995) J Am Chem Soc 117: 11898;
20. b) Hoch U, Adam W, Fell RT, Saha-Möller CR, Schreier P (1997) J Mol Cat A: Chemical 117: 321;
21. c) Adam W, Humpf HU, Korb M, Schreier P (1997) Tetrahedron Asymm 8: 3555
22. Schjanberg P (1937) Z Phys Chem A 179: 32
23. Tseng CY, Hall JB, Vock MH, Vinals JF, Shuster EJ, Hruza DE (1976) GE Patent 2530227
24. Dodd DS, Oehlschlager AC, Georgopapadakou NH, Polak AM, Hartman PG (1992) J Org Chem 57: 7226
25. Smith AB, Levenberg PA (1981) Synthesis 567