A Mechanistic Alternative for the Intramolecular Hydroboration of Homoallylic Amine and Phosphine Borane Complexes
- 6 August 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (35) , 10502-10503
- https://doi.org/10.1021/ja034655m
Abstract
Intramolecular hydroboration is demonstrated starting from homoallylic amine boranes upon activation by iodine. The process involves a B-iodoborane complex as the intermediate and may occur via internal displacement of iodide by the alkene to generate a cationic borane-alkene π-complex on the way to hydroboration products. The reaction can be carried out using a catalytic amount of iodine.Keywords
This publication has 12 references indexed in Scilit:
- Substrate-directable chemical reactionsChemical Reviews, 1993
- Diastereoselectivity in the borane methyl sulfide promoted hydroboration of .alpha.-alkoxy-.beta.,.gamma.-unsaturated esters. Documentation of an alkoxy-directed hydroboration reactionThe Journal of Organic Chemistry, 1992
- Determinations of transition-state geometries by the endocyclic restriction test: mechanisms of substitution at nonstereogenic atomsAccounts of Chemical Research, 1992
- Highly stereoselective synthesis of 1,3-diols utilizing intramolecular hydroboration of allyl vinyl ethersJournal of the Chemical Society, Chemical Communications, 1989
- Rhodium(I)-catalyzed hydroboration of olefins. The documentation of regio- and stereochemical control in cyclic and acyclic systemsJournal of the American Chemical Society, 1988
- Mechanism of hydroboration in ether solvents. A model ab initio studyJournal of the Chemical Society, Chemical Communications, 1983
- Hydroboration. XXXII. Cyclic hydroboration of dienes with thexylboraneJournal of the American Chemical Society, 1972
- Synthesis of asymmetric boron cations and resolution with As(C6H4P2)3- anionJournal of the American Chemical Society, 1968
- Über einige 1,1-Dimethyl-1,2-azaboracycloalkaneCollection of Czechoslovak Chemical Communications, 1968
- Über eine aussergewöhnliche Stereospezifität bei der Hydroborierung der diastereomeren (1R)‐Isopulegole mit DiboranHelvetica Chimica Acta, 1967