Asymmetric synthesis of 1-aryl and 1,3-diarylcyclopentenes by the Heck reaction of 1-sulfinylcyclopentenes with iodoarenes

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4107-4111

  De La Rosa, Juan Carlos ^a   Díaz, Nuria ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Asymmetric synthesis; Cyclopentenes; Heck reaction; Palladium; Sulfoxides

Indexed keywords

CYCLOPENTENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS; TECHNIQUE;

EID: 0343674560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00579-7     Document Type: Article

References (26)

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2. Recent reviews of Heck and related reactions: (a) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
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8. Reviews on the asymmetric Heck reaction: (a) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
9. (b) Guiry, P. J.; Hennessy, A. J.; Cahill, J. P. Top. Catal. 1997, 4, 311.
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12. 3CN, rt) of o-aminophenyl disulfide, which was prepared by oxidation of o-iodoaniline according to a reported procedure (
13. Trisubstituted alkenes are rarely used in intermolecular Heck reactions due to their scarce reactivity. For a review on the insertion of transition metal alkyl complexes on alkenes, see: Soderberg, B. C. In Comprehensive Organometallic Chemistry II; Vol. 3, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995; pp. 241-297. See also: Hillers, S. O.; Reiser, O. Synlett 1995, 153.
14. Trisubstituted alkenes are rarely used in intermolecular Heck reactions due to their scarce reactivity. For a review on the insertion of transition metal alkyl complexes on alkenes, see: Soderberg, B. C. In Comprehensive Organometallic Chemistry II; Vol. 3, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, 1995; pp. 241-297. See also: Hillers, S. O.; Reiser, O. Synlett 1995, 153.
15. The Heck products of cyclopentene are very prone to suffer C=C bond migration in the presence of the palladium catalysts. For examples of Heck reactions of cyclopentene, see: (a) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
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20. 3 (figures below). On the other hand, this stereochemical assignment was confirmed by chemical correlation of optically pure 2B (3R, SR configuration) into (S) 3-phenylcyclopentene (Scheme 3).The high reactivity and stereoselectivity of the tribustituted alkenes 1-4 in Heck reactions could be attributed to a intramolecular like process facilitated by the previous coordination of the dimethylamino group to the palladium cationic species prior to the insertion step (see graphic for (R)-1 and Ref. 4a). For the participation of Pd-N coordinated complexes in the Heck reaction of amino olefins, see: Larhed, M.; Andersson, C.; Hallberg, A. Tetrahedron 1994, 50, 285 (and references cited therein).
21. -3.
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25. 3).
26. Julia, M.; Fabre, J. L. Tetrahedron Lett. 1983, 24, 4311. All attempts to remove the chiral auxiliary by reaction with other desulfurizating agents (activated zinc, Al-Hg, Na-Hg or Raney nickel) were unsuccessful due to the lack of reactivity or formation of mixtures of products.