Palladium-Catalyzed Intramolecular δ-Lactam Formation of Aryl Halides and Amide-Enolates:  Syntheses of Cherylline and Latifine

Honda, Toshio; Namiki, Hidenori; Satoh, Fumie

doi:10.1021/ol0155337

Cited by 75 publications

(27 citation statements)

References 15 publications

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“…194 Analogous reaction conditions were then used by these authors to convert carboxyamide 141 into lactam 142, which was used as a precursor to alkaloid latifine (Scheme 59). 194 In 2001, it was also shown by Lee and Hartwig that a catalyst system composed of a 1:1 mixture of Pd(OAc) 2 and PCy 3 or a sterically hindered N-heterocyclic carbene ligand provides fast rates for the synthesis of oxindoles 134 by R-arylation of o-bromoanilides 133 or the corresponding o-chloro derivatives at 50-70°C in the presence of NaOtBu as the base.…”

Section: Synthesis Of R-arylated Carboxyamides and Lactamsmentioning

confidence: 99%

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

2009

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Section: Synthesis Of R-arylated Carboxyamides and Lactamsmentioning

confidence: 99%

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

2009

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“…202 Nevertheless, the addition of arylboronic reagents to aryl nitroalkenes is inefficient in the area of stereoselective catalysis and the development of potent catalysts for this transformation is still in demand. 203,204 Excellent progress was accomplished by Lin et al, who employed a C2-symmetric chiral diene as a ligand and potassium trifluoroborates as organoboron reagents, which were created in situ, to obtain good to excellent ee. In this light, a highly efficient transformation was reported regarding the Rh/sulfoxide-phosphine-catalyzed enantioselective addition of diverse arylboronic acids to 2-nitrostyrenes under mild reaction conditions to obtain the desired products with excellent ee.…”

Section: Table 48mentioning

confidence: 99%

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Heravi

Dehghani

Zadsirjan

2016

Tetrahedron: Asymmetry

106

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Rh-catalyzed asymmetric 1,4-addition reactions to a,b-unsaturated carbonyl and related compounds: an update Available online xxxx Dedicated to my son, OMID on the occasion of his 35th birthday. a b s t r a c tThe Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to an appropriate receptor has been a growing area of research over the last decade. The receptors for such a 1,4-addition reaction are chiefly a,b-unsaturated ketones, esters, amides, enones, nitroalkenes, and occasionally phosphonates etc. This reaction in the presence of chiral rhodium complexes introduce the aryl and alkenyl groups at the b-position of the above electron poor olefins, enantioselectively. Chiral Rh complexes similar to other transition metals can be added to some electron poor olefins, in turn making them viable to attack by various organometallic reagents for highly enantioselective C-C bond formation. The Rh-catalyzed asymmetric 1,4-addition of organometallic reagents to electron poor olefins has been reviewed in 2003. Due to the importance of the asymmetric C-C bond formation via 1,4-conjugate addition reactions and the number of such reactions catalyzed by Rh-complexes, in this review we highlight the recent advances in Rh-complex asymmetric catalyzed 1,4-addition reactions since 2003.

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“…Intramolecular reaction of an amide-enolate and palladium catalyst was used in the synthesis of cherylline and latifine [31] (Scheme 17).…”

Section: Sp 3 ( Carbonyl)-sp 2 : Heck Reaction and Othersmentioning

confidence: 99%

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

Hong¹,

Nimje

2006

COC

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The development of new catalytic reactions for C-C bond formation has played a significant role in natural products synthesis. In this article we review catalytic C-C bond formation with respect to the carbon atoms' hybridization and the products formed. The reactions of unusual substrates and the development of new reaction conditions and catalyst systems are included. This survey highlights the use of catalysts in natural products synthesis during the years 2000-2005.

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Palladium-Catalyzed Intramolecular δ-Lactam Formation of Aryl Halides and Amide-Enolates: Syntheses of Cherylline and Latifine

Abstract: [reaction: see text] Palladium-catalyzed intramolecular carbon-carbon bond formation of aryl halides and amide-enolates gave 4-arylisoquinoline derivatives in good yields, which were further converted into the isoquinoline alkaloids cherylline and latifine.

Cited by 75 publications

References 15 publications

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

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Palladium-Catalyzed Intramolecular δ-Lactam Formation of Aryl Halides and Amide-Enolates: Syntheses of Cherylline and Latifine

Abstract: [reaction: see text] Palladium-catalyzed intramolecular carbon-carbon bond formation of aryl halides and amide-enolates gave 4-arylisoquinoline derivatives in good yields, which were further converted into the isoquinoline alkaloids cherylline and latifine.

Cited by 75 publications

References 15 publications

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update

Catalytic C-C Bond Formation in Natural Products Synthesis: Highlights From The Years 2000 – 2005

Contact Info

Product

Resources

About

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides