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200517.fm Page 155 Friday, March 18, 2005 2:52 PM
2005
Benzopyran derivatives
R 0350
Regio- and Diastereoselective Insertion of Allenes into Stable Oxapalladacycles
a Metal-Bonded Stereogenic Carbon. Preparation of Contiguously Substitut17- 141 with
ed 3,4-Dihydro-2H-1-Benzopyrans. — Coupling of the oxapalladacycles (I) with
electron-rich allenes offers a convenient approach to 2,3-disubstituted 3,4-dihyrobenzopyrans. Steric and electronic parameters of the allenes strongly affect the regio- and
stereoselective outcome. The reaction proceeds with 60-90% retention of stereochemical information indicating predominant formation of C-bonded palladium enolate
intermediates rather than O-bonded analogues. — (LU, G.; MALINAKOVA*, H. C.;
J. Org. Chem. 69 (2004) 24, 8266-8279; Dep. Chem., Univ. Kans., Lawrence,
KS 66045, USA; Eng.) — Jannicke
200517.fm Page 156 Friday, March 18, 2005 2:52 PM
2005
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