We are grateful for financial support from the Swedish Research Council, the Swedish Foundation for Strategic Research, and the Ministerio de Educación y Ciencia of Spain.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
You have free access to this content
Highly Compatible Metal and Enzyme Catalysts for Efficient Dynamic Kinetic Resolution of Alcohols at Ambient Temperature†
Article first published online: 1 DEC 2004
DOI: 10.1002/anie.200461416
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Martín-Matute, B., Edin, M., Bogár, K. and Bäckvall, J.-E. (2004), Highly Compatible Metal and Enzyme Catalysts for Efficient Dynamic Kinetic Resolution of Alcohols at Ambient Temperature. Angew. Chem. Int. Ed., 43: 6535–6539. doi: 10.1002/anie.200461416
- †
Publication History
- Issue published online: 1 DEC 2004
- Article first published online: 1 DEC 2004
- Manuscript Received: 23 JUL 2004
- 1For examples, see:
- 1a
- 1b
- 1c
- 2For chemoenzymatic DKR, see:
- 2a
- 2b
- 2c
- 2d
- 2e
- 2f, Angew. Chem. 1997, 109, 1221–1222;Angew. Chem. Int. Ed. Engl. 1997, 36, 1173–1174.Direct Link:Direct Link:
- 3
- 4
- 5
- 5a, , , Angew. Chem. 1997, 109, 1256–1258;Angew. Chem. Int. Ed. Engl. 1997, 36, 1211–1212;Direct Link:Direct Link:
- 5b
- 6
- 7
- 7a
- 7b
- 7c
- 7d
- 8
- 8a
- 8b
- 9
- 10
- 11
- 12
- 12a
- 12b, , , Proc. Natl. Acad. Sci. USA 2004, 101, 5761–5766;
- 12cB. Martín-Matute, J.-E. Bäckvall, J. Org. Chem., in press.
- 13
- 14
- 14a
- 14b
- 15
- 16
- 17
- 17a, , , , , , Angew. Chem. 2002, 114, 2479–2482;Angew. Chem. Int. Ed. 2002, 41, 2373–2376;Direct Link:Direct Link:
- 17b
- 18
- 19Immobilized and commercially available as Novozym-435.
- 20Under the same reaction conditions, (2-naphthyl)-1-ethanol gave (2-naphthyl)-1-ethanol acetate in 100 % yield but 0 % ee.
- 21To avoid opening of the reaction vessel, the order of addition of reagents was changed slightly: Toluene was added to a mixture of KOtBu, Ru complex, CALB, and Na2CO3. After 6 min the alcohol was added and the mixture was stirred for 4 min. Finally, isopropenyl acetate was added.
- 22To control the water activity, the enzyme was stored in a sealed container with a saturated solution of LiCl for a minimum of 24 h. An excess of KOtBu is needed to consume the water in the reaction mixture. To test this hypothesis, DKR of 4 a was carried out under the same reaction conditions as in Table 1, entry 4, but employing 40 mg of CALB instead of 6 mg. Acetate 5 a was obtained in only 57 % yield after 3 h.
- 23
- 23a, Chem. Eur. J. 2004, 10, 2366–2374, and references therein;Direct Link:
- 23b
- 24
- 25
- 26NMR data can be found in the following references: 5 a: , , , J. Org. Chem. 1988, 53, 5531–5535; 5 b: , , , Tetrahedron 1995, 51, 3235–3246; 5 c: , , Synth. Commun. 1991, 21, 1721–1727; 5 d: , , , Tetrahedron: Asymmetry 1993, 4, 813–822; 5 e: , , , , , J. Org. Chem. 2000, 65, 83–88; 5 f: , , , Tetrahedron: Asymmetry 2002, 13, 815–820; 5 h: reference [5b]; 7: , , , J. Org. Chem. 1992, 57, 5231–5239.
- 27Stirring for 10 min gave essentially the same result but stirring for 1.5 h gave less-reproducible results.