Diastereofacial Selectivity of Enolates

Journal of Organic Chemistry

Volumn 52, Issue 21, 1987, Pages 4681-4686

  Mccarthy, Peter A ^a   Kageyama, Masanori ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012876697     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00230a005     Document Type: Article

References (15)

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2. Masamune, S.; Ali, Sk. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
3. Masamune, S.; McCarthy, P. A. In Macrolide Antibiotics; Omura, S., Ed.; Academic: New York, 1984; p 127. Masamune, S.; Choy, W. Aldrichimica Acta 1982, 15, 47. Paterson, I.; Mansuri, M. M. Tetrahedron 1985. 41. 3569.
4. Evans, D. A.; Nelson, J. V.; Taber, T. R. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; Wiley-Inster-science: New York, 1982; p 1 and references cited therein. Evans, D. A. Aldrichimica Acta 1982, 15, 23 and references cited therein.
5. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York. 1983: Vol. 2. and references cited therein.
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7. McCarthy, P. A. Tetrahedron Lett. 1982, 23, 4199.
8. Designation of an enolate's diastereomeric face is made by using a variation of the re,si system: Hanson, K. R. J. Am. Chem. Soc. 1966, 88, 2731. All designations ae made with regard to the oxygen-bearing carbon of the enolate moiety. The priority order is oxygen, the sp5carbon, and then the sp2 carbon. Such designations refer to the same absolute face of all enolates regardless of enolate geometry or substitution.
9. Masamune, S.; Ellingboe, J. W.; Choy, W. J. Am. Chem. Soc. 1982, 104, 5526. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
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