Enantiopure β-hydroxy morpholine amides from terminal epoxides by carbonylation at 1 atm

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4703-4705

  Goodman, Steven N ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Amides; Carbonylation; Cobalt; Epoxides; Homogeneous catalsis

Indexed keywords

ACYLATION; HYDROXYLATION; OXIDES; SYNTHESIS (CHEMICAL);

MORPHOLINE AMIDES;

CARBONYLATION;

AMIDE; CARBON MONOXIDE; CARBONYL DERIVATIVE; EPOXIDE; ESTER DERIVATIVE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MORPHOLINE; MORPHOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENANTIOMER; METHODOLOGY; PRESSURE; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

AMIDES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; MORPHOLINES; STEREOISOMERISM;

EID: 0037122049     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290022     Document Type: Article

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27. For a review of synthetic approaches to the HMG-CoA reductase inhibitors up to 1986, see: a) T. Rosen, C. H. Heathcock, Tetrahedron 1986, 42, 4909-4951; for selected, more recent examples of routes to these intermediates, see: b) G. Beck, H. Jendralla, K. Kesseler, Synthesis 1995, 1014-1018; (c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361; (d) J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837-838; (e) D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669-685; (f) "Synthesis of the Common Lactone Moiety of HMG-CoA Reductase Inhibitors": I. M. McFarlane, C. G. Newton, P. Pitchen in Process Chemistry in the Pharmaceutical Industry (Ed.: K. G. Gadamasetti), Dekker, New York, 1999, pp. 243-259.
28. For a review of synthetic approaches to the HMG-CoA reductase inhibitors up to 1986, see: a) T. Rosen, C. H. Heathcock, Tetrahedron 1986, 42, 4909-4951; for selected, more recent examples of routes to these intermediates, see: b) G. Beck, H. Jendralla, K. Kesseler, Synthesis 1995, 1014-1018; (c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361; (d) J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837-838; (e) D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669-685; (f) "Synthesis of the Common Lactone Moiety of HMG-CoA Reductase Inhibitors": I. M. McFarlane, C. G. Newton, P. Pitchen in Process Chemistry in the Pharmaceutical Industry (Ed.: K. G. Gadamasetti), Dekker, New York, 1999, pp. 243-259.
29. For a review of synthetic approaches to the HMG-CoA reductase inhibitors up to 1986, see: a) T. Rosen, C. H. Heathcock, Tetrahedron 1986, 42, 4909-4951; for selected, more recent examples of routes to these intermediates, see: b) G. Beck, H. Jendralla, K. Kesseler, Synthesis 1995, 1014-1018; (c) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361; (d) J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837-838; (e) D. A. Evans, M. C. Kozlowski, J. A. Murry, C. S. Burgey, K. R. Campos, B. T. Connell, R. J. Staples, J. Am. Chem. Soc. 1999, 121, 669-685; (f) "Synthesis of the Common Lactone Moiety of HMG-CoA Reductase Inhibitors": I. M. McFarlane, C. G. Newton, P. Pitchen in Process Chemistry in the Pharmaceutical Industry (Ed.: K. G. Gadamasetti), Dekker, New York, 1999, pp. 243-259.