Bimetallic catalytic cascade ring closing metathesis—intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst

Grigg, Ronald; York, Mark

doi:10.1016/s0040-4039(00)01250-8

Cited by 68 publications

(26 citation statements)

References 9 publications

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“…293,294 In a telescoped sequence, bridged lactams 124a and 118a were prepared from simple acyclic starting materials in a one-pot transformation. 294 This methodology was also employed for the synthesis of analogous bridged sulfonamides (see Section 6.5). 291–294 More recently, Paquette reported the synthesis of [4.3.1], [3.3.2] and [4.3.2] bridged lactams via Heck reaction utilizing similar conditions to those reported by Grigg (Scheme 31).…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

“…294 This methodology was also employed for the synthesis of analogous bridged sulfonamides (see Section 6.5). 291–294 More recently, Paquette reported the synthesis of [4.3.1], [3.3.2] and [4.3.2] bridged lactams via Heck reaction utilizing similar conditions to those reported by Grigg (Scheme 31). 295 The enamide substrates were synthesized by RCM of acyclic dienes, again providing an efficient route to bridged lactams.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

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Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

Section: Synthesis Of Bridged Lactams With N–(co) Bond On Two-carbmentioning

confidence: 99%

Chemistry of Bridged Lactams and Related Heterocycles

2013

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“…Ligand 29 (Table 15.1, entry 9) was also used in intramolecular Mizoroki-Heck reactions [72]. In combination with Pd(OAc) 2 , it catalysed a cascade ring-closing metathesis (RCM)/Mizoroki-Heck reaction.…”

Section: Fluorous Phasementioning

confidence: 99%

Mizoroki–Heck Reactions: Modern Solvent Systems and Reaction Techniques

Bonrath¹,

Létinois²,

Netscher³

et al. 2009

The Mizoroki–Heck Reaction

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“…Separation of triphenylphosphine oxide from the TPP reaction usually requires chromatography. Recently, PS-TPP [11] and F-TPP [12] have been used to simplify the byproduct separation process. The Lindsley group studied the Staudinger reaction using F-TPP 8 and two polymeric TPPs with cross-linked polystyrene 9a and cross-linked NovaGel™ 9b, respectively [13].…”

Section: Resultsmentioning

confidence: 99%

Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison

Chen

Zhang

2005

Mol Divers

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SummaryReactions using fluorous reagents and scavengers are compared side-by-side with their solidsupported counterparts. Fluorous triphenylphosphine is used in the bromination reaction of alcohols, fluorous thiol is used as an electrophile scavenger for α-bromoketones, fluorous isatoic anhydride is used as a nucleophile scavenger for primary and secondary amines. Reactions involving fluorous reagents and scavengers occur in homogeneous media with solution-phase reaction kinetics. Reactions with solid-supported reagents and scavengers occur in a heterogeneous media, and the reaction kinetics is greatly affected by the nature of the solid-support and reaction environment. Significantly larger amounts of reagents and longer time are usually needed to complete the solidsupported reaction.

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Bimetallic catalytic cascade ring closing metathesis—intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst

Cited by 68 publications

References 9 publications

Chemistry of Bridged Lactams and Related Heterocycles

Chemistry of Bridged Lactams and Related Heterocycles

Mizoroki–Heck Reactions: Modern Solvent Systems and Reaction Techniques

Fluorous reagents and scavengers versus solid-supported reagents and scavengers, a reaction rate and kinetic comparison

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