Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3193-3196

  Högberg, Hans Erik ^a   Lindmark, Marica ^a   Isaksson, Dan ^a   Sjödin, Kristina ^a   Franssen, Maurice C R ^b   Jongejan, Hugo ^b   Wijnberg, Joannes B P A ^b   De Groot, Aede ^b  

^a MID SWEDEN UNIVERSITY   (Sweden)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Hemiacetal ester; Hindered alcohol; Lipase

Indexed keywords

ACETAL DERIVATIVE; ACETALDEHYDE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; TRIACYLGLYCEROL LIPASE; VINYL ACETATE;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; ENZYME MECHANISM; ESTERIFICATION; STEREOSPECIFICITY;

EID: 0038709784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00328-2     Document Type: Article

References (18)

1. (a) Faber, K. In Biotransformations in Organic Chemistry; Springer Verlag: Germany, 3rd ed., 1997.
2. (b) Anderson, E. M.; Larsson, K. M.; Kirk, O. Biocatal. Biotransform. 1998, 16, 181-204.
3. (c) Rotticci, D.; Hæffner, F.; Orrenius, C.; Norin, T.; Hult, K. J. Mol. Catal. B, Enzymatic 1998, 5, 267-272.
4. (a) Nordin, O.; Nguyen, B.-V.; Vörde, C.; Hedenström, E.; Högberg, H.-E. J. Chem. Soc., Perkin Trans. 1 2000, 367-376.
5. (b) Franssen, M. C. R.; Jongejan, H.; Kooijman, H.; Spek, A. L.; Camacho Mondril, N. L. F. L.; Boavida dos Santos, P. M. A. C.; De Groot, A.E. Tetrahedron: Asymmetry 1996, 7, 497-510.
6. (c) Enzymatic Reactions in Organic Media; Koskinen, A. M. P.; Klibanov, A. M., Eds.; Blackie: UK, 1996.
7. Osprian, I.; Steinreiber, A.; Mischitz, M.; Faber, K. Biotechnol. Lett. 1996, 18, 1331-1334.
8. Franssen, M. C. R.; Jongejan, H.; Kooijman, H.; Spek, A. L.; Bell, R. P. L.; Wijnberg, J. B. P. A.; De Groot, A.E. Tetrahedron: Asymmetry 1999, 10, 2729-2738.
9. (a) Lindmark, M.; Isaksson, D.; Sjödin, K.; Högberg, H.-E., in press.
10. (b) Compound 2 can be efficiently resolved by acylation with vinyl acetate catalysed by Candida rugosa lipase (CRL) in diisopropyl ether (Ref. 4) and is a key intermediate for the synthesis of the marasmane and lactarane sesquiterpenes: see: Ref. 4 and Bell, R. P. L.; Sobolev, A.; Wijnberg, J. B. P. A.; De Groot, A.E. J. Org. Chem. 1998, 63, 122-128.
11. ™ L6 and Novozyme 435 gave (-)-1-Ac (E~2) and (+)-1-Ac (E~1.5), respectively.
12. (a) Franssen, M. C. R.; Goetheer, E. L. V.; Jongejan, H.; De Groot, Ae. Tetrahedron Lett. 1998, 39, 8345-8348.
13. (b) Angelis Y.S.; Smnou, I. Tetrahedron Lett. 1997, 38, 8109-8112.
14. (c) ibid 1998, 39, 2823-2826.
15. Boiled in water for 5 min, after which the water was removed by evaporation in vacuo.
16. The enantiopreference of CALB in this reaction is opposite to that of Candida rugosa lipase in the formation of 2-Ac (Ref. 4).
17. Many lipases hydrolyse vinyl acetate, even under 'dry' conditions: Weber, H. K.; Weber, H.; Kazlauskas R. J. Tetrahedron: Asymmetry 1999, 10, 2635-2638.
18. 3COOH): 174.1045; found: 174.1041.