Alkenylation of allylic alcohols using alkenylboron dihalides: A formal transition-metal free Suzuki reaction

Chemical Communications

Volumn , Issue 19, 2005, Pages 2492-2494

  Kabalka, George W ^a   Yao, Min Liang ^a   Borella, Scott ^a   Wu, Zhongzhi ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALLYL ALCOHOL; ALLYL COMPOUND; ALLYLIC HYDROXIDE; BORON DERIVATIVE; CARBON; HALIDE; HYDROXIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ALKENYLATION; ALKYLATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; TECHNIQUE;

EID: 20044381293     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502026c     Document Type: Article

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47. At this time, the experimental evidence cannot be used to identify whether the migration of the vinyl group to the allylic center occurs with inversion, retention, or racemization. Analogous studies involving chiral benzylic alcohols (unpublished results) strongly support the formation of cationic intermediates which would lead to epimerization at the migration terminus. Further studies using chiral allylic alcohols are underway.