Enantioselective introduction of a benzenesulfonylmethyl substituent at an unactivated carbon atom via chemoenzymatic methods

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7459-7462

  Maguire, Anita R ^a   Kelleher, Leonard L ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; CYCLOPENTANONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; YEAST;

EID: 0030759893     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01756-5     Document Type: Article

References (30)

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4. A few reports of the unusual combination of transition metal catalysis and biocatalysis in organic synthesis have appeared recently e.g. Allen, J.V.; Williams, J.M.J. Tetrahedron Lett., 1996, 37, 1859; Dinh, P.M.; Howarth, J.A.; Hudnott, A.R.; Williams, J.M.J.; Harris, W. Tetrahedron Lett., 1996, 37, 7623; Backvall, J.-E. Acta Chem. Scand., 1996, 50, 661.
5. A few reports of the unusual combination of transition metal catalysis and biocatalysis in organic synthesis have appeared recently e.g. Allen, J.V.; Williams, J.M.J. Tetrahedron Lett., 1996, 37, 1859; Dinh, P.M.; Howarth, J.A.; Hudnott, A.R.; Williams, J.M.J.; Harris, W. Tetrahedron Lett., 1996, 37, 7623; Backvall, J.-E. Acta Chem. Scand., 1996, 50, 661.
6. A few reports of the unusual combination of transition metal catalysis and biocatalysis in organic synthesis have appeared recently e.g. Allen, J.V.; Williams, J.M.J. Tetrahedron Lett., 1996, 37, 1859; Dinh, P.M.; Howarth, J.A.; Hudnott, A.R.; Williams, J.M.J.; Harris, W. Tetrahedron Lett., 1996, 37, 7623; Backvall, J.-E. Acta Chem. Scand., 1996, 50, 661.
7. Rhodium catalysed C-H insertion reactions to form cyclopentanone derivatives were originally developed by Taber using α-diazo-β-keto esters, Taber, D.F.; Petty, E.H J. Org. Chem., 1982, 47, 4808, and later extended to α-diazo-β-keto sulfones, Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Monteiro, H.J.; Zukerman-Schpector, J. Tetrahedron, 1996, 52, 3879.
8. Rhodium catalysed C-H insertion reactions to form cyclopentanone derivatives were originally developed by Taber using α-diazo-β-keto esters, Taber, D.F.; Petty, E.H J. Org. Chem., 1982, 47, 4808, and later extended to α-diazo-β-keto sulfones, Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Monteiro, H.J.; Zukerman-Schpector, J. Tetrahedron, 1996, 52, 3879.
9. Rhodium catalysed C-H insertion reactions to form cyclopentanone derivatives were originally developed by Taber using α-diazo-β-keto esters, Taber, D.F.; Petty, E.H J. Org. Chem., 1982, 47, 4808, and later extended to α-diazo-β-keto sulfones, Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Monteiro, H.J.; Zukerman-Schpector, J. Tetrahedron, 1996, 52, 3879.
10. Rhodium catalysed C-H insertion reactions to form cyclopentanone derivatives were originally developed by Taber using α-diazo-β-keto esters, Taber, D.F.; Petty, E.H J. Org. Chem., 1982, 47, 4808, and later extended to α-diazo-β-keto sulfones, Monteiro, H.J. Tetrahedron Lett., 1987, 28, 3459; Kennedy, M.; McKervey, M.A.; Maguire, A.R.; Roos, G.H.P. J. Chem. Soc., Chem. Commun., 1990, 361; Monteiro, H.J.; Zukerman-Schpector, J. Tetrahedron, 1996, 52, 3879.
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28. Full details of the optimisation of the yeast mediated kinetic resolutions will be reported elsewhere.
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