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Lipase catalyzed ac...
Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres : the resolution of (± ) -4,4 -dimethyl -3 -phenyl -1 -pentanol
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- Sabbani, Sunil (författare)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Hedenström, Erik (författare)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Andersson, Jimmy (författare)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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(creator_code:org_t)
- Elsevier BV, 2007
- 2007
- Engelska.
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Ingår i: Tetrahedron. - : Elsevier BV. - 0957-4166 .- 1362-511X. ; 18:14, s. 1712-1720
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- Enantioselective acylation of some (±)-3-alkyl-3-phenyl-l-propanols was performed with enzymes as catalysts. Moderate enantiomeric ratios (E), ranging up to E = 11.6, were obtained. In the resolution, some of the lipases selectively acylated the (+)-enantiomer while others acylated the (-)-enantiomer of the γ-substituted primary alcohols 1-4. Thus, it is possible to obtain both enantiomers of the alcohols as remaining substrate with high enantiomeric purity. The resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol 4 was extensively studied and screening experiments were conducted to select suitable lipase(s), reaction medium, acyl donor and appropriate temperature combinations to increase the enantiomeric ratio. Chirazyme® L-6/chloroform/vinyl propionate/38 °C and Chirazyme® L-7/di-iso-propyl ether/vinyl propionate/0 °C were chosen to obtain both enantiomers, (R)-(+)-4 and (S)-(-)-4, respectively, via sequential resolutions in excellent enantiomeric excess (>98%) and in 25% and 22% yield, respectively.
Ämnesord
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Nyckelord
- Chemistry
- Kemi
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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