Pd-catalyzed cross-coupling reaction of (Z)- and (E)-bromoenyne: Unusual stereochemical outcome

Tetrahedron Letters

Volumn 46, Issue 2, 2005, Pages 225-228

  Uenishi, Jun'ichi ^a   Matsui, Katsuaki ^a   Ohmi, Masashi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Bromoenyne; Enediyne; Sonogashira coupling; Stereocontrol; Stille coupling

Indexed keywords

ALKYNE DERIVATIVE; BROMOENYNE; PALLADIUM; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 10044285173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.061     Document Type: Article

References (14)

1. Excellent books for Pd chemistry E.-i. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis Vols. 1 and 2 2002 John Wiley & Sons New York
2. J. Tsuji Perspectives in Organopalladium Chemistry for the XXI Century 1999 Elsevier Amsterdam
3. K. Sonogashira B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 521 550
4. D.W. Knight B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 481 520
5. K. Tamao B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 435 480
6. F. Diederich P.J. Stang Metal-Catalyzed Cross-coupling Reactions 1998 Wiley-VCH Weinheim
7. Tan, Z.; Negishi E. in Ref. a, Vol. 1, pp 863-942
8. J. Uenishi, and K. Matsui Tetrahedron Lett. 42 2001 4353 4355
9. J. Uenishi, K. Matsui, and A. Wada Tetrahedron Lett. 44 2003 3093 3096
10. Treatment of 2E and 2Z with an excess of diimide generated from dipotassium diazodicarboxylate with acetic acid in THF, reduced trimethylsilylethynyl function chemoselectively to trimethylsilylethyl function, respectively. Their geometries were determined by the NOE experiments, shown below. This protocol was reported previously, see: J. Uenishi, K. Matsui, and H. Ohmiya J. Organomet. Chem. 653 2002 141 149
11. 3 (selected) 1Z δ 0.22 (9H, s), 1.05 (9H, s), 4.34 (2H, d, J = 5.3 Hz), 6.55 (1H, t, J = 5.3 Hz). 1E δ 0.10 (9H, s), 1.56 (9H, s), 4.32 (2H, d, J = 6.6 Hz), 6.46 (1H, t, J = 6.6 Hz)
12. To our best knowledge, this is a quite rare example except one. The isomerization of (E)- and (Z)-1-alkynyl-1-alkenyl lithium via cummlenyl lithium intermediate was proposed and methylation of bromoenyne was reported without a description of the detail. See: J.A. Miller, W. Leong, and G. Zweifel J. Org. Chem. 53 1988 1839 1840
13. o-Benzylidenylimino group instead of ortho amino group also induced a similar stereochemical result
14. 2 catalyzed alkylation of 3-bromo-3-en-1-yne with alkylzinc reagent took place with retention of the configuration. J. Shi, X. Zeng, and E. Negishi Org. Lett. 5 2003 1825 1828