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Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic alpha-Amino Amides
-
- Blid, Jan (author)
- KTH,Kemi
- Brandt, Peter (author)
-
- Somfai, Peter (author)
- KTH,Kemi
- (creator_code:org_t)
- 2004-03-27
- 2004
- English.
- In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 69:9, s. 3043-3049
- Journal article (peer-reviewed)
Abstract
Subject headings
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- Boron trifluoride and BBr3 mediated [2,3]-sigmatropic rearrangements of allylic alpha-amino amides have been developed affording secondary amines in good yields. (E)-Crotyl and (E)-cinnamyl alpha-amino amides 2b and 2c exhibit excellent syn-diastereoselectivity upon rearrangement with either Lewis acid. The allylic amine 2a forms upon treatment with BF3 or BBr3 a five-membered heterocylic complex in which a single halide anion has been displaced by the carbonyl oxygen atom. The structures of the Lewis acid-amine complexes were elucidated using NMR spectroscopy. A plausible reaction mechanism, based on DFT calculations, is presented. Thus, BF3- or BBr3-complexed allylic amines 2 are shown to preferentially proceed, after deprotonation, via an endo transition state.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- Complexation
- Nuclear magnetic resonance spectroscopy
- Oxygen
- Probability density function
- Reaction kinetics
- Stereochemistry
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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