Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration

Chemical Communications

Volumn 3, Issue 19, 2003, Pages 2482-2483

  Hirai, Atsushi ^a   Yu, Xiao Qiang ^a   Tonooka, Terumichi ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL BORONIC ACID; BORONIC ACID DERIVATIVE; ESTER; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; QUANTUM YIELD; RING OPENING; STEREOSPECIFICITY;

EID: 0142042815     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b307390d     Document Type: Article

References (6)

1. B. M. Kim, S. F. Williams and S. Masamune, in Comprehensive Organic Synthesis, Additions to C—X π-Bonds, Part 2, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, ch. 1.7
2. H. Hayakawa, N. Okada, M. Miyashita, Tetrahedron Lett., 1999, 40, 3191
3. A. Hirai, T. Tonooka, K. Wakatsuki, K. Tanino, M. Miyashita, Chirality, 2003, 15, 108
4. T. Suzuki, O. Sato, M. Hirama, Tetrahedron Lett., 1990, 31, 4747
5. L. Wang, K. B. Sharpless, J. Am. Chem. Soc., 1992, 114, 7568
6. D. Xu, G. A. Crispino, K. B. Sharpless, J. Am. Chem. Soc., 1992, 114, 7570