Book ChapterDOI
Metal homoenolates from siloxycyclopropanes
Isao Kuwajima,Eiichi Nakamura +1 more
TLDR
The potential of metal homoenolates as multifunctional reagents in organic synthesis has become recognized in the last decade as mentioned in this paper, and a review summarizes the research activities of homoenolate chemistry.Abstract:
The potential of metal homoenolates as multifunctional reagents in organic synthesis has become recognized in the last decade. Ring opening of siloxycyclopropanes by Lewis acidic metals currently provides the best route to the metal homoenolates, which are either isolable as a stable complex or exist only as a transient organometallic species. This review summarizes, for the first time, the research activities of metal homoenolate chemistry. Other synthetically useful routes to metal homoenolates are also described.read more
Citations
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Journal ArticleDOI
Selective Carbon–Carbon Bond Cleavage of Cyclopropanols
TL;DR: This review highlights new developments in this area over the past two decades of carbon-carbon (C-C) bond cleavage of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.
Journal ArticleDOI
C-acylation of cyclopropanols: preparation of functionalized 1,4-diketones.
TL;DR: A convenient method for preparing attractively functionalized 1,4-diketones has been devised by palladium-catalyzed cross-coupling of cyclopropanols and acyl chlorides by demonstrating the utility in an enantioselective synthesis of (+)-myrmicarin 217.
Journal ArticleDOI
Palladium-mediated ring opening of hydroxycyclopropanes
Soon-Bong Park,Jin Kun Cha +1 more
TL;DR: In this paper, the palladium-mediated ring opening of substituted cyclopropanols has been found to take place predominantly at the less substituted C−C bond, which is the same as the case of the titanium-medication of esters.
Journal ArticleDOI
Aerobic oxidation of organic compounds catalyzed by vanadium compounds
TL;DR: Aerobic oxidation of α-hydroxy ketones catalyzed by dichloroethoxyoxovanadium in ethanol causes a carbon-carbon bond cleavage that produces diesters or diketones as discussed by the authors.
Journal ArticleDOI
Diastereodivergent Carbometalation/Oxidation/Selective Ring Opening: Formation of All‐Carbon Quaternary Stereogenic Centers in Acyclic Systems
TL;DR: The developed title reaction sequence allows the preparation of both enantiomers of aldehyde (VIb) starting from the same initial cyclopropene derivative [(S)-Ib] as mentioned in this paper.
References
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Journal ArticleDOI
Methods of Reactivity Umpolung
TL;DR: There are six principal methods of umpolung: 1 2n-oxidation, heteroatom exchange and modification, homologation and its reversal, the cyclopropane “trick”, use of acetylenes, and redox reactions; under certain circumstances none of these techniques is necessary in cases where direct umpoline is possible.
Journal ArticleDOI
Perfluoroalkanesulfonic esters: methods of preparation and applications in organic chemistry
Journal ArticleDOI
Transition metal catalyzed rearrangements of small ring organic molecules.
Journal ArticleDOI
Evidence for a reversible d, π-complexation, β-cupration sequence in the conjugate addition reaction of Gilman reagents with α,β-enones.
E. J. Corey,Neil W. Boaz +1 more
TL;DR: In situ trapping of reaction intermediates combined with stereochemical studies of the reaction of lithium dimethylcuprate with enones provides evidence for a pathway involving d,π-cuprate-enone and copper(III) β-adducts as important intermediates in cuprate-mediated conjugate addition of carbon.
Book
Organotitanium Reagents in Organic Synthesis
TL;DR: In this paper, the authors discuss the use of Titanium in organic chemistry and present a list of some of the main uses of the material in the field of organic chemistry, including: 1.1.