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Diastereoselective addition of organozinc reagents to 2-alkyl-3-(arylsulfanyl)propanals
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- Larsson, Michael (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Galandrin, Elodie (author)
- Mittuniversitetet
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- Högberg, Hans-Erik (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
- (creator_code:org_t)
- Elsevier BV, 2004
- 2004
- English.
- In: Tetrahedron. - : Elsevier BV. - 0040-4020 .- 1464-5416. ; 60:47, s. 10659-10669
- Journal article (peer-reviewed)
Abstract
Subject headings
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- The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R = Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl]pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl]dodecanal and Me2Zn in the presence of TiCl4.
Subject headings
- NATURVETENSKAP -- Kemi -- Oorganisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Inorganic Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- diastereoselective additions
- dimethylzinc
- titanium tetrachloride
- chelation
- pheromones
- Inorganic chemistry
- Oorganisk kemi
- Chemistry
Publication and Content Type
- ref (subject category)
- art (subject category)
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- Articles in the publication
- Tetrahedron
- By the university
- Royal Institute of Technology
- Mid Sweden University
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