Ring Opening in the Hydrostannation of Methylenecyclopropanes:  Effect of the Catalyst and Substrate

Lautens, Mark; Meyer, Christophe; Lorenz, Alexander

doi:10.1021/ja962582j

Cited by 108 publications

(55 citation statements)

References 37 publications

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“…The mechanism is based upon those proposed by Greeves, [27] Gevorgyan, [28] and Lautens. [29] Oxidative addition of Bu 3 SnH to Pd 0 provides Pd II complex A. Coordination of the triple bond with A leads to complex B, which may then undergo insertion of the triple bond to the Pd-H bond to give vinylpalladium(II) complex C followed by reductive elimination to furnish vinylstannane 4.…”

mentioning

confidence: 99%

Stereoselective Synthesis of Difunctionalized 1,3‐Dienes Containing Tin and Sulfonyl Groups by Palladium‐Catalyzed Regio‐ and Stereocontrolled Addition Reactions

Zhao¹,

Yang²,

Xie³

et al. 2011

Eur J Org Chem

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Using palladium‐catalyzed addition reactions, a terminal alkyne, an acetylenic sulfone, and a tin hydride comprise the building blocks for the construction of difunctionalized 1,3‐dienes containing tin and sulfonyl groups in an atom‐economical fashion. Terminal alkynes 1 undergo clean cis addition to acetylenic sulfones 2 in the presence of catalytic amounts of palladium acetate and tri(2,6‐dimethoxyphenyl)phosphane to give (E)‐1‐sulfonyl‐substituted 1,3‐enynes 3 in excellent yields. Hydrostannylation of 1,3‐enynes 3 with tributyltin hydride in the presence of Pd(PPh3)4 affords regio‐ and stereoselectively (1E,3E)‐1‐sulfonyl‐3‐tributylstannyl‐substituted 1,3‐dienes 4 in excellent yields.

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mentioning

confidence: 99%

Stereoselective Synthesis of Difunctionalized 1,3‐Dienes Containing Tin and Sulfonyl Groups by Palladium‐Catalyzed Regio‐ and Stereocontrolled Addition Reactions

Zhao¹,

Yang²,

Xie³

et al. 2011

Eur J Org Chem

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“…The corresponding ring-opened homoallylstannanes were obtained in good to excellent yields and as single diastereomers (Scheme 3). [13] The relative stereochemistry of homoallylstannane 15 corresponds to that of the parent compound 14, establishing that there is no loss of the stereochemical information initially present in the (methylenecyclopropyl)carbinol 14 throughout the course of the reaction. The same reaction could also be successfully applied to alkylidenecyclopropane derivatives Scheme 2.…”

Section: Discussionmentioning

confidence: 93%

Selectivity in Metal‐Catalyzed CarbonCarbon Bond Cleavage of Alkylidenecyclopropanes

Masarwa

Marek

2010

Chemistry A European J

207

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When more complex system leads to simpler reactivity profile; the ring-opening of strained three-membered rings such as methylene- and alkylidenecyclopropanes generally lead to several products. If one starts with more functionalized carbon skeletons, selective reactions are now observed and rationalization as well as synthetic applications are described in this concept article. This methodology could be used to the preparation of challenging structural motifs possessing quaternary carbon stereocenters in acyclic systems.

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“…[23] As explained in Scheme 3, the hydrostannation of the methylenecyclopropanes 1h and 1i exclusively proceeded through proximal bond cleavage.…”

Section: Reviewsmentioning

confidence: 98%

Transition Metal-Catalyzed Reactions of Methylenecyclopropanes

Nakamura

Yamamoto

2002

Advanced Synthesis & Catalyis

353

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Ring Opening in the Hydrostannation of Methylenecyclopropanes: Effect of the Catalyst and Substrate

Cited by 108 publications

References 37 publications

Stereoselective Synthesis of Difunctionalized 1,3‐Dienes Containing Tin and Sulfonyl Groups by Palladium‐Catalyzed Regio‐ and Stereocontrolled Addition Reactions

Stereoselective Synthesis of Difunctionalized 1,3‐Dienes Containing Tin and Sulfonyl Groups by Palladium‐Catalyzed Regio‐ and Stereocontrolled Addition Reactions

Selectivity in Metal‐Catalyzed CarbonCarbon Bond Cleavage of Alkylidenecyclopropanes

Transition Metal-Catalyzed Reactions of Methylenecyclopropanes

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