Broadly Effective Enantioselective Diels-Alder Reactions of 1-Amino-substituted-1,3-butadienes

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1163-1164

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

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

BUTADIENES; CYCLIZATION; INDICATORS AND REAGENTS; STEREOISOMERISM; TEMPERATURE;

EID: 0037018443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0255716     Document Type: Article

References (42)

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4. Of the successful (>90% ee, see ref 1c) DA's reported, the vast majority involve the use of cyclopentadiene, butadiene, or their alkyl-substituted derivatives.
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10. For reactions involving mono-alkoxy- or -acyloxy-substituted butadienes, see: (a) Marshall, J. A.; Xie, S. J. J. Org. Chem. 1992, 57, 2987-2989.
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24. The sole example of a Lewis acid-catalyzed enantioselective DA reaction of a simple amino-substituted diene (i.e., of the Oppolzer-Overman type) predating our work was that of Evans, who observed high enantioselectivity for the cycloaddition between N-Cbz-amino-1,3-butadiene and N-acrolyloxazolidinone. The latter is capable of two-point binding to the chiral catalyst. See: Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582-7594.
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35. The synthetic significance of the present work stems from the paucity of enantioselective DA reactions of amine-substituted butadienes and the demonstrated usefulness of 1-aminobutadiene Diels-Alder reactions in natural product synthesis. See reports cited in ref 3. See also: (a) Chigr, M.; Fillion, H.; Rougny, A. Tetrahedron Lett. 1987, 28, 4529-4532.
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41. Cr(III)-(salen) catalyst was used in enantioselective hetero-Diels-Alder reactions by Jacobsen: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403-405.
42. Welker has reported the use of Jacobsen's salen as a stoichiometric chiral auxiliary for dienes: Chapman, J. J.; Day, C. S.; Welker, M. E. Eur. J. Org. Chem. 2001, 2273-2282 and references therein.