Stereoselective Synthesis of Homoallylic Alcohols by Migratory Insertion    Reactions of Higher-Order Cyanocuprates and Nickel-Catalysed Coupling Reactions Involving Enol Carbamates

Kocieński, Philip; Dixon, N. J.

doi:10.1055/s-1989-34703

Cited by 8 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, Kocienski and Dixon developed the first effective Ni(0)-catalyzed cross-coupling of vinyl carbamates with organomagnesium reagents in 1989, 21 and several years later Snieckus and coworkers described the Ni(0)-catalyzed cross-coupling of aryl carbamates and organomagnesium reagents in concert with further functionalization by directed ortho -metallation. 22 Subsequently, Snieckus also reported the Ni(0)-catalyzed cross-coupling of tertiary aryl sulfamates with organomagnesium reagents.…”

Section: Cross-couplingmentioning

confidence: 99%

Recent advances in homogeneous nickel catalysis

Tasker

Standley

Jamison

2014

Nature

1,997

1,098

View full text Add to dashboard Cite

Preface The field of nickel catalysis has made tremendous advances in the past decade. There are several key properties of nickel that have allowed for a broad range of innovative reaction development, such as facile oxidative addition and ready access to multiple oxidation states. In recent years, these properties have been increasingly understood and leveraged to perform transformations long considered exceptionally challenging. Herein, we discuss some of the most recent and significant developments in homogeneous nickel catalysis with an emphasis on both synthetic outcome and mechanism.

show abstract

Section: Cross-couplingmentioning

confidence: 99%

Recent advances in homogeneous nickel catalysis

Tasker

Standley

Jamison

2014

Nature

1,997

1,098

View full text Add to dashboard Cite

show abstract

“…The earliest examples of carbamate coupling were described by Kocienski and Dixon in 1989 460. The authors found that a vinyl carbamate substrate could be coupled with alkyl Grignard reagents in the presence of Ni II precatalysts (Scheme 156).…”

Section: Nickel-catalyzed Cross-couplings Of Aryl and Vinyl Carbammentioning

confidence: 99%

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

et al. 2010

View full text Add to dashboard Cite

“…Other approaches have been reported, where the triple bond is built from a particular homoallyl alcohol bearing a chlorine 21,22 or a carbamate 9,23 on the double bond. Finally the base-catalyzed ring-opening of vinyl oxetanes has also been described.…”

Section: Biographical Sketchesmentioning

confidence: 99%

Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems

Ferreira¹,

Denichoux²,

Chemla³

et al. 2004

Synlett

View full text Add to dashboard Cite

The results of our research dealing with the stereoselective synthesis of propargylic and homopropargylic systems are summarized. In a first part, the stereoselective formation of syn-or anti-disubstituted homopropargylic alcohols from acetylenic oxiranes through S N 2 or double S N 2¢ has been developed. Thus, the two diastereomers of a given homopropargylic alcohol are stereospecifically available. The great impact of Lewis acid activation on the regioselectivity of the ring-opening reactions of propargylic oxiranes is also detailed. In a second part, the preparation and uses of new acetylenic/allenic carbenoids are overviewed; their reactivity towards carbonyl compounds and imines is examined, leading to the highly stereoselective synthesis of acetylenic chlorohydrins, oxiranes and aziridines.

show abstract

Stereoselective Synthesis of Homoallylic Alcohols by Migratory Insertion Reactions of Higher-Order Cyanocuprates and Nickel-Catalysed Coupling Reactions Involving Enol Carbamates

Cited by 8 publications

References 0 publications

Recent advances in homogeneous nickel catalysis

Recent advances in homogeneous nickel catalysis

Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen Bonds

Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems

Contact Info

Product

Resources

About