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Synthesis of tetrah...
Synthesis of tetrahydroisoquinoline (TIQ)-oxazoline ligands and their application in enantioselective Henry reactions
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Kawthekar, Rahul B. (author)
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Chakka, Sai Kumar (author)
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Francis, Vivian (author)
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- Andersson, Pher G (author)
- Uppsala universitet,Institutionen för biokemi och organisk kemi
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Kruger, Hendrik G. (author)
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Maguire, Glenn E. M. (author)
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Govender, Thavendran (author)
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(creator_code:org_t)
- Elsevier BV, 2010
- 2010
- English.
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In: Tetrahedron. - : Elsevier BV. - 0957-4166 .- 1362-511X. ; 21:7, s. 846-852
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- A novel family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide beta-hydroxy nitroalkanes in high conversion (>99%) This paper describes the synthesis of the TIQ compounds from L-dihydroxyphenylalanine (L-DOPA) as the starting material The chiral ligands were complexed in situ with various transition metals such as Cu, Sc, Co, Zn, Ni and Mn and tested as a chiral catalyst for the Henry reaction The reaction was optimized in terms of the metal, counter ion, solvent, temperature and over a range of substrates The corresponding catalyst with copper(II) acetate and 2-propanol as the solvent provides the best enantioselectivities (up to 77% ee) of the corresponding nitroalcohol for 4-chlorobenzaldehyde.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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