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Braddock DC, MacGilp ID, Perry BG. Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol. J Org Chem. 2002;67(24):8679-81doi: 10.1021/jo020451x.
Braddock, D. C., MacGilp, I. D., & Perry, B. G. (2002). Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol. The Journal of organic chemistry, 67(24), 8679-81. https://doi.org/10.1021/jo020451x
Braddock, D Christopher, et al. "Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol." The Journal of organic chemistry vol. 67,24 (2002): 8679-81. doi: https://doi.org/10.1021/jo020451x
Braddock DC, MacGilp ID, Perry BG. Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol. J Org Chem. 2002 Nov 29;67(24):8679-81. doi: 10.1021/jo020451x. PMID: 12444659.
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J Org Chem. 2002 Nov 29;67(24):8679-81. doi: 10.1021/jo020451x.

Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol.

The Journal of organic chemistry

D Christopher Braddock, Iain D MacGilp, Benjamin G Perry

Affiliations

  1. Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, SW7 2AY UK. [email protected]

PMID: 12444659 DOI: 10.1021/jo020451x

Abstract

(+/-)-4,12-Dihydroxy[2.2]paracyclophane [(+/-)-PHANOL] is readily prepared from [2.2]paracyclophane by an improved synthetic protocol. Enzymatic kinetic resolution of its bis-acetate proceeds with good enantioselection. Separation, hydrolysis, and recrystallization provides both enantiomers of PHANOL in high enantiopurity.

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