Assembly of 3a-Arylperhydroindoles by the Intramolecular Cycloaddition of 2-Azaallyl Anions with Alkenes. Total Syntheses of (±)-Crinine, (±)-6-Epicrinine, (-)-Amabiline, and (-)-Augustamine

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3607-3617

  Pearson, William H ^a   Lovering, Frank E ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001731905     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972255+     Document Type: Article

References (42)

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3. Portions of this work have appeared in communication form: (a) Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173-9176. (b) Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 12336-12337.
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20. The analysis given neglects the possible stereoelectronic contributions resulting from the interaction of the alkene with the allylic ether. While the effect of allylic ethers on the stereoselectivity of addition of electrophiles to alkenes has been studied extensively, the effect of such a substituent on the stereoselectivity of the addition of nucleophiles to alkenes has received much less attention. Studies on the diastereoselectivity of 2-azaallyl anions with simpler allylic ethers are planned in our laboratories. For leading references on the 1,2asymmetric induction in the addition of electrophiles to alkenes, see: (a) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1700. For leading references on the 1,2-asymmetric induction in the addition of nucleophiles to alkenes, see: (b) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129.
21. The analysis given neglects the possible stereoelectronic contributions resulting from the interaction of the alkene with the allylic ether. While the effect of allylic ethers on the stereoselectivity of addition of electrophiles to alkenes has been studied extensively, the effect of such a substituent on the stereoselectivity of the addition of nucleophiles to alkenes has received much less attention. Studies on the diastereoselectivity of 2-azaallyl anions with simpler allylic ethers are planned in our laboratories. For leading references on the 1,2asymmetric induction in the addition of electrophiles to alkenes, see: (a) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698-1700. For leading references on the 1,2-asymmetric induction in the addition of nucleophiles to alkenes, see: (b) Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129.
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39. 13C NMR, IR, and mass spectra of natural amabiline for comparison.
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