Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral α,α-disubstituted 1,3-propanediols

Tetrahedron Asymmetry

Volumn 8, Issue 2, 1997, Pages 283-291

  Fadel, Antoine ^a   Arzel, Philippe ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 PROPANEDIOL; APHANORPHINE; EPTAZOCINE;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HYDROLYSIS; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0031026294     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00500-9     Document Type: Article

References (25)

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2. (b) Fadel, A.; Garcia-Argote, S. Tetrahedron: Asymmetry 1996, 7, 1159.
3. (c) Fadel, A.; Canet, J.-L.; Salaün, J. Synlett 1991, 60.
4. (d) Canet, J.-L.; Fadel, A.; Salaün, J. J. Org. Chem. 1992, 57, 3463.
5. (e) Fadel, A.; Canet, J.-L.; Salaün, J. Tetrahedron: Asymmetry 1993, 4, 27.
6. Fadel, A.; Arzel, Ph. Tetrahedron: Asymmetry 1995, 6, 893.
7. (a) For specialized books see: Poppe, L.; Novák, L. Selective Biocatalyis: a Synthetic Approach VCH: Weinheim 1992; for reviews see:
8. (b) Boland, W.; Forössl, C.; Lorenz, M. Synthesis 1991, 1049.
9. (c) Banfi, L.; Guanti, G. Synthesis 1993, 1029-1056.
10. (d) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17.
11. (e) Schoffers, E.; Golebiowski, A.; Johnson, C.R. Tetrahedron 1996, 52, 3769-3826 and references cited therein.
12. (a) Green, F.R. III.; Olyslager, R.J.E. Eur. Patent. Appl. EP 280.232 (1988), CA 1989, 110, 37813h.
13. (b) Ehler, J.; Seebach, D. Liebigs Ann. Chem. 1990, 379.
14. (c) Suemune, H.; Harabe, T.; Xie, Z.F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337.
15. Therisod, M.; Klibanov, A.M. J. Am. Chem. Soc. 1986, 108, 5638 and references cited therein.
16. Bovara, R.; Carrera, G.; Ferrara, L.; Riva, S. Tetrahedron: Asymmetry 1991, 2, 931.
17. 3.
18. See ref. 4(a).
19. Alkylation of 8b with 2-(2-bromoethyl)-1,3-dioxane and its transformation into 10 gave roughly the same yield.
20. Very recently the diester 10 was used to prepare the corresponding chiral acid ester according to refs 2 and 3 by enzymatic hydrolysis with PLE see, Hallinan, K.O.; Honda, T. Tetrahedron 1996, 51, 12211.
21. 3N greatly enhanced the reaction rate, see: Theil, F.; Ballschuh, S.; Schick; H.; Haupt, M.; Hafner, B.; Schwarz, S. Synthesis 1988, 540.
22. Under acidic conditions the (R)-(+)-2 underwent racemisation into (±)-2 by the 1,5-rearrangement of the acyl function.
23. 3).
24. Hulme, A.N.; Henry, S.S.; Meyers, A.J. J. Org. Chem. 1995, 60, 1265.
25. Allevi, P.; Ciuffreda, P.; Tarocco, G.; Anastasia, M. J. Org. Chem. 1996, 61, 4144.