Diene Cyclization toward Chiral Acyliminium Ions

The Grignard reaction of 10-bromo-7-methyldeca-2, 6-diene (5) with a C2-symmetric chiral imide 1gave a corresponding hydroxy lactam 6 in 67% yield. Acid cyclization of 6 gave chiral carbocycles 7 and 8 in 53 and 15% yields, respectively. The stereochemistry of 8 was deduced by the NOE and CD spectra...

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Published inNippon Kagakukai shi (1972) Vol. 1996; no. 4; pp. 416 - 418
Main Authors ENDO, Akihisa, FUNATSU, Masashi, INOUYE, Yoshinobu
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 1996
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Summary:The Grignard reaction of 10-bromo-7-methyldeca-2, 6-diene (5) with a C2-symmetric chiral imide 1gave a corresponding hydroxy lactam 6 in 67% yield. Acid cyclization of 6 gave chiral carbocycles 7 and 8 in 53 and 15% yields, respectively. The stereochemistry of 8 was deduced by the NOE and CD spectra of the derived ketone 10. In a similar manner, the acid cyclization of the hydroxy lactam 12, prepared from the bromide 5 and a chiral imide 11, afforded a chiral carbocycle, which was purified as an acetate 13 in 27% yield. The stereochemistry of 13 was confirmed by correlating to that of 8.
ISSN:0369-4577
2185-0925
DOI:10.1246/nikkashi.1996.416