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Diastereoselective addition of chiral azomethine ylides to cyclic alpha,beta-unsaturated N-enoylbornanesultams
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- Karlsson, Staffan (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Högberg, Hans-Erik (author)
- Mittuniversitetet,Institutionen för naturvetenskap (-2008)
- (creator_code:org_t)
- 2002-03-15
- 2002
- English.
- In: Journal of the Chemical Society. Perkin Transactions 1. - : Royal Society of Chemistry (RSC). - 1472-7781 .- 1364-5463. ; 2002:8, s. 1076-1081
- Journal article (peer-reviewed)
Abstract
Subject headings
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- Doubly diastereoselective 1,3-dipolar cycloaddition reactions of chiral non-racemic azomethine ylides to cyclic five-and six-membered α,β-unsaturated N-enoylbornanesultams were carried out. When suitable solvents were used, the fused bicyclic adducts formed were obtained in good diastereoselectivity. Moreover, a change of the absolute configuration of the starting ylide precursor reversed the diastereoselectivity of some such reactions. Cleavage of the chiral auxiliary of the cycloadducts furnished amino alcohols and a β-amino ester. The latter was transformed into a known precursor of an antibacterial compound.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- 1
- 3-dipolar cycloaddition
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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