Alkynylborinates in organoborane conversions

Soderquist, John A.; Rane, Anil; Matos, Karl; Ramos, Jorge

doi:10.1016/0040-4039(95)01444-m

Cited by 24 publications

(10 citation statements)

References 18 publications

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“…The Pd-catalyzed alkynylation reactions with alkynylmetals containing Mg, 15,21 B, 15 Al, 15,22,23 and Sn 15 were also reported by Negishi in 1978, even though the B 15,[24][25][26][27] and Sn 15,28,29 versions have sometimes been labeled as the Suzuki and Stille alkynylation reactions, respectively. More systematic investigations of Pd-catalyzed alkynylation with alkynylstannanes were performed in the early 1980s by Bumagin, Beletskaya, and their co-workers 28 and later by Stille.…”

Section: Introduction: Historical Perspective and Overview Of The mentioning

confidence: 85%

Palladium-Catalyzed Alkynylation

2003

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Section: Introduction: Historical Perspective and Overview Of The mentioning

confidence: 85%

Palladium-Catalyzed Alkynylation

2003

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“…The cross-coupling proceeds mechanistically by the characteristic pathway of oxidative-addition, transmetallation, and reductive-elimination affording the product while regenerating the active catalyst. Soderquist and coworkers have also developed alkynylborinates 86, designed for cross-coupling, which allow easier isolation than their 9-BBN counterparts 84 [216].…”

Section: Rxmentioning

confidence: 99%

Cross‐Coupling Reactions to sp Carbon Atoms

Marsden¹,

Haley²

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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“…This result indicates that both the 1,2-metallate rearrangement and the transmetallation take place at a surprisingly low temperature. It is noteworthy that the protonolysis of vinyl boranes is typically performed with acetic acid at 0 °C 65,66…”

Section: Resultsmentioning

confidence: 99%

One-Pot Multicomponent Coupling Methods for the Synthesis of Diastereo- and Enantioenriched (Z)-Trisubstituted Allylic Alcohols

et al. 2009

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Abstract(Z)-Trisubstituted allylic alcohols are widespread structural motifs in natural products and biologically active compounds but are difficult to directly prepare. Introduced herein is a general one-pot multicomponent coupling method for the synthesis of (Z)-α,α,β-trisubstituted allylic alcohols. (Z)-Trisubstituted vinylzinc reagents are formed in situ by initial hydroboration of 1-bromo-1-alkynes. Addition of dialkylzinc reagents induces a 1,2-metallate rearrangement that is followed by a boron-to-zinc transmetallation. The resulting vinylzinc reagents add to a variety of prochiral aldehydes to produce racemic (Z)-trisubstituted allylic alcohols. When enantioenriched aldehyde substrates are employed (Z)-trisubstituted allylic alcohols are isolated with high dr (>20:1 in many cases). For example, vinylation of enantioenriched benzyl protected α-and β-hydroxy propanal derivatives furnished the expected anti-Felkin addition products via chelation control. Surprisingly, silyl protected α-hydroxy aldehydes also afford anti-Felkin addition products. A protocol for the catalytic asymmetric addition of (Z)-trisubstituted vinylzinc reagents to prochiral aldehydes with a (−)-MIB-based catalyst has also been developed. Several additives were investigated as inhibitors of the Lewis acidic alkylzinc halide byproducts, which promote the background reaction to form the racemate. α-Ethyl and α-cyclohexyl (Z)-trisubstituted allylic alcohols can now be synthesized with excellent levels of enantioselectivity in the presence of diamine inhibitors.

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Alkynylborinates in organoborane conversions

Cited by 24 publications

References 18 publications

Palladium-Catalyzed Alkynylation

Palladium-Catalyzed Alkynylation

Cross‐Coupling Reactions to sp Carbon Atoms

One-Pot Multicomponent Coupling Methods for the Synthesis of Diastereo- and Enantioenriched (Z)-Trisubstituted Allylic Alcohols

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