CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL

LANGER K, Mattay J (1995)
The Journal of Organic Chemistry 60(22): 7256-7266.

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This work deals with copper(I)-catalyzed intramolecular [2 + 2]-photocycloadditions of 1,6-diene derivatives. The bridgehead carbons C-l and C-5 of the resulting bicyclo[3.2.0]heptanes are generated stereoselectively by using chiral starting material, chiral catalysts, or chiral auxiliaries. The irradiation of (S)-3 leads to enantiomerically pure 4 and 5 which opens a new synthetic route to enantiomerically pure (+)- and (-)-grandisol 9. The use of chiral copper complexes as catalysts delivers enantiomeric excesses below 5%. The reason for these small excesses is a low reactivity of the chiral copper complexes, as confirmed by CD-spectroscopic measurements. Malic acid or amino carboxylic acid derivatives as chiral auxiliaries yield the bicyclic alcohols 4 and 5 with enantiomeric excesses up to 15%. The employment of a chiral diol as an auxiliary delivers a chiral ketal 36, and the resulting ketone 7 exhibits enantiomeric excesses up to 60%.
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LANGER K, Mattay J. CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL. The Journal of Organic Chemistry. 1995;60(22):7256-7266.
LANGER, K., & Mattay, J. (1995). CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL. The Journal of Organic Chemistry, 60(22), 7256-7266.
LANGER, K., and Mattay, J. (1995). CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL. The Journal of Organic Chemistry 60, 7256-7266.
LANGER, K., & Mattay, J., 1995. CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL. The Journal of Organic Chemistry, 60(22), p 7256-7266.
K. LANGER and J. Mattay, “CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL”, The Journal of Organic Chemistry, vol. 60, 1995, pp. 7256-7266.
LANGER, K., Mattay, J.: CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL. The Journal of Organic Chemistry. 60, 7256-7266 (1995).
LANGER, K, and Mattay, Jochen. “CYCLOADDITIONS .55. STEREOSELECTIVE INTRAMOLECULAR COPPER(I)-CATALYZED [2+2]-PHOTOCYCLOADDITIONS - ENANTIOSELECTIVE SYNTHESIS OF (+)-GRANDISOL AND (-)-GRANDISOL”. The Journal of Organic Chemistry 60.22 (1995): 7256-7266.
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