Highly enantioselective Diels-Alder reactions of 1-amino-3-siloxy-dienes catalyzed by Cr(III)-salen complexes [17]

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7843-7844

  Huang, Yong ^a   Iwama, Tetsuo ^a   Rawal, Viresh H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHROMIUM; CHROMIUM DERIVATIVE; SOLVENT;

CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; LETTER; MOLECULAR SIZE; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0034674921     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002058j     Document Type: Letter

References (36)

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17. Enantioselective hetero-Diels-Alder reactions of Danishefsky's diene have been reported: (a) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405. (b) Simonsen, K. B.; Svenstrup, N.; Robertson, M.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 123-128 and references therein.
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26. (a) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897-5898. Although catalysis of a Diels-Alder reaction using a Cr salen catalyst has not been reported, catalysis of hetero-Diels-Alder reactions is known: see ref 8a.
27. 10b,f (Formula Presented)
28. 2. The filtrate was concentrated and the residue purified by flash chromatography on silica gel.
29. 6 in MTBE for ∼5 h followed by removal of the precipitated AgCl and concentration of the solution (see also ref 8a).
30. The corresponding Mn(III)-salen complex is also effective in catalyzing the DA reaction, but affords lower enantioselectivities. Oxo(Mn)-salen complexes are known to catalyze the asymmetric DA reactions of cyclopentadiene and acroleins: Yamashita, Y.; Katsuki, T. Synlett 1995, 829-830.
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35. The carboxylate group on the nitrogen is expected to be oriented s-trans to the diene during the DA reactions, see: (a) Menezes, R. F.; Zezza, C. A.; Sheu, J.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3295-3298.
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