Amino acid-derived enaminones: A study in ring formation providing valuable asymmetric synthons

Journal of the American Chemical Society

Volumn 128, Issue 27, 2006, Pages 8702-8703

  Turunen, Brandon J ^a   Georg, Gunda I ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID; ENAMINE; ENAMINONE; UNCLASSIFIED DRUG;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CHIRALITY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

AMINO ACIDS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 1-RING; HETEROCYCLIC COMPOUNDS, 2-RING; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33745950245     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0609046     Document Type: Article

References (24)

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7. For examples in which an intermediate enaminone or related structure is then converted to a bicycle, see: (b) refs 2a and 2b.
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18. Retro-Michael and retro-Mannich-type processes have been reported previously on β-amino ketones. For examples, see: (a) Slosse, P.; Hootele, C. Tetrahedron 1981, 37, 4287-4294.
19. (b) Morley, C.; Knight, D. W.; Share, A. C. J. Chem. Soc., Perkin Trans. 1 1994, 2903-2907.
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21. Diastereomeric conversion in these examples (22 and 23) may be explained by simple enolization.
22. Studies are underway to clearly determine how this protocol is able to suppress the diastereomeric interconversion.
23. 2) could account for these observations. (Diagram presented)
24. When ynone 2 was subjected to reaction conditions, near quantitative conversion to 30 was observed (eq 3). (Diagram presented)