Stereocontrolled solution and solid phase enolate alkylations and hydroxylations - Generation of three and four contiguous stereogenic carbon atoms in acyclic systems

Tetrahedron Letters

Volumn 40, Issue 25, 1999, Pages 4631-4634

  Hanessian, Stephen ^a   Ma, Jianguo ^a   Wang, Wengui ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

1,2 asymmetric induction; Enolate alkylation; Polypropionate synthesis; Solid phase chemistry

Indexed keywords

ALLYL COMPOUND; BENZYL DERIVATIVE; CARBON; HALIDE; POLYPROPIONIC ACID; POTASSIUM DERIVATIVE; POTASSIUM ENOLIC ACID; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CONJUGATION; HYDROXYLATION; STEREOCHEMISTRY;

EID: 0033581031     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00782-0     Document Type: Article

References (26)

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3. 1. For three diverse approaches, see for example, Kokke, W. C. M. C.; Varkevisser, F. A. J. Org. Chem. 1974, 39, 1535; Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668; Corey, E. J.; Peterson, R. T. Tetrahedron Lett. 1985, 26, 5025.
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6. 3. For excellent summaries, see Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: New York, 1996; p. 75; Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC: New York, 1995; p. 97; for a selection of early seminal individual contributions, see Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 1; Lutomsky, K. A.; Meyers, A. I. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 213; Oppolzer, W. Tetrahedron 1987, 43, 1969, 4057.
7. 3. For excellent summaries, see Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: New York, 1996; p. 75; Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC: New York, 1995; p. 97; for a selection of early seminal individual contributions, see Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 1; Lutomsky, K. A.; Meyers, A. I. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 213; Oppolzer, W. Tetrahedron 1987, 43, 1969, 4057.
8. 3. For excellent summaries, see Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: New York, 1996; p. 75; Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC: New York, 1995; p. 97; for a selection of early seminal individual contributions, see Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 1; Lutomsky, K. A.; Meyers, A. I. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 213; Oppolzer, W. Tetrahedron 1987, 43, 1969, 4057.
9. 3. For excellent summaries, see Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis; Pergamon: New York, 1996; p. 75; Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology; CRC: New York, 1995; p. 97; for a selection of early seminal individual contributions, see Evans, D. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 1; Lutomsky, K. A.; Meyers, A. I. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: Orlando, 1984; Vol. 3, p. 213; Oppolzer, W. Tetrahedron 1987, 43, 1969, 4057.
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20. 10. Hanessian, S.; Huynh, H. K. Tetrahedron Lett. 1999, 40, 671; For related papers, see Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733, 737; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835.
21. 10. Hanessian, S.; Huynh, H. K. Tetrahedron Lett. 1999, 40, 671; For related papers, see Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733, 737; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835.
22. 10. Hanessian, S.; Huynh, H. K. Tetrahedron Lett. 1999, 40, 671; For related papers, see Hanessian, S.; Xie, F. Tetrahedron Lett. 1998, 39, 733, 737; Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5835.
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26. 13C NMR spectra are available upon request.