Catalytic asymmetric synthesis of quaternary carbon centers: Investigation of intramolecular Heck reactions and the application to calabar alkaloid synthesis

Chemtracts

Volumn 12, Issue 4, 1999, Pages 289-296

  Iserloh, U ^a   Curran, D P ^a   Overman, L E ^b,b   Bachand, B ^b   Poon, D J ^b   Calter, M A ^b   Govek, S P ^b   Matsuura, T ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; NOTE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0008415425     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Note

References (21)

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2. First described by (a) Sato, Y., Sodeoka, M., Shibasaki, M. J. Org, Chem. 1989, 54, 4738 (b) Carpenter, N.E., Kucera, D.J., Overman, L.E. J. Org. Chem. 1989, 54, 5846.
3. For general reviews: (a) Jeffery, T. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 153 (b) de Meijere, A., Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379 (c) Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2. For reviews on the AHR: (d) Shibasaki, M. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 119 (e) Shibasaki, M., Boden, C.D.J., Kojima, A. Tetrahedron 1997, 53, 7371.
4. For general reviews: (a) Jeffery, T. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 153 (b) de Meijere, A., Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379 (c) Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2. For reviews on the AHR: (d) Shibasaki, M. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 119 (e) Shibasaki, M., Boden, C.D.J., Kojima, A. Tetrahedron 1997, 53, 7371.
5. For general reviews: (a) Jeffery, T. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 153 (b) de Meijere, A., Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379 (c) Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2. For reviews on the AHR: (d) Shibasaki, M. In Advances in Metal-Organic Chemistry, Liebeskind, L.S., ed., JAI Press: Greenwich, 1996, vol. 5, p. 119 (e) Shibasaki, M., Boden, C.D.J., Kojima, A. Tetrahedron 1997, 53, 7371.
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11. 2 = H) rationalizes not only the observed reversal of stereoselectivity upon switching from the Z- to E-alkene precursor, but also the intrinsically higher ee's observed with Z-alkene precursors: see ref. 40-42 in Ashimori, A., Bachand, B., Calter, M.A., Govek, S.P., Overman, L.E., Poon, D.J. J. Am. Chem. Soc. 1998, 120, 6488.
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13. In the presence of a chiral Pd-complex, this isomerization can lead to an effective kinetic resolution, enhancing the enantiomeric excess of 7:(a) Ozawa, F., Kubo, A., Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417 (b) Hayashi, T., Kubo, A., Ozawa, F. Pure Appl. Chem. 1992, 64, 421 (c) Ozawa, F., Kobatake, Y., Hayashi, T. Tetrahedron Lett. 1993, 34, 2505.
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