Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
نویسندگان
چکیده
منابع مشابه
Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if β-migratory insertion proceeds faster than direct cross-coupling, an additional carbon-carbon bond and stereocenter can be formed. With the aid of a nick...
متن کاملStereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones
The development of efficient methods for the generation of enantioenriched sulfonamides and sulfones is an important objective for fields such as organic synthesis and medicinal chemistry; however, there have been relatively few reports of direct catalytic asymmetric approaches to controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-ca...
متن کاملAnalysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions.
The use of tpy'(tpy'= 4,4',4''-tri-tert-butyl-terpyridine) as a ligand for nickel allows for the isolation of a Ni(I)-alkyl complex and a Ni(II)-alkyl halide complex, both of which can be used as mechanistic probes of key steps in alkyl cross-coupling reactions.
متن کاملEvidence for a NiI active species in the catalytic cross-coupling of alkyl electrophiles.
Addition of terpyridine to (TMEDA)Ni(CH3)2 results in the high-yield formation of (terpyridyl)NiMe (3). This NiI organometallic complex was found to be capable of transferring its methyl group to iodocyclohexane to produce methylcyclohexane in high yield. Compound 3 can also serve as an initiator for the catalytic cross-coupling of alkyl electrophiles performed under Negishi-like conditions.
متن کاملCatalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic
We have developed a nickel-catalyzed method for the asymmetric cross-coupling of secondary electrophiles with secondary nucleophiles, specifically, stereoconvergent Negishi reactions of racemic benzylic bromides with achiral cycloalkylzinc reagents. In contrast to most previous studies of enantioselective Negishi cross-couplings, tridentate pybox ligands are ineffective in this process; however...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2014
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja500706v