Stereocontrolled Preparation of a Nonpeptidal (−)-Spirobicyclic NK-1 Receptor Antagonist

Maligres, Peter E.; Waters, Marjorie M.; Lee, Jaemoon; Reamer, Robert A.; Askin, David; Ashwood, Michael S.; Cameron, Mark

doi:10.1021/jo0157472

Cited by 32 publications

(17 citation statements)

References 14 publications

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“…Preparation of the starting compounds : Allyl bromide ( 12 a ), crotyl chloride ( 12 b ), and 3‐chloro‐2‐methylpropene ( 12 c ) were commercially available. 3‐Bromo‐2‐butylpropene ( 12 d ),30 3‐bromo‐2‐phenylpropene ( 12 e ),31 and 2‐bromomethyl acrylic acid ethyl ester ( 12 f )32 were prepared according to the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

Double Ring‐Closing Metathesis Reaction of Nitrogen‐Containing Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives

2004

Chemistry A European J

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The double ring-closing metathesis reaction of nitrogen-containing tetraenes was studied. The selectivity of the fused/dumbbell-type products can be controlled by the electronic/steric effects of the substituents attached to the C[double bond]C bonds and the s-cis/s-trans conformational ratios of the substrates. This methodology has also been successfully applied to the enantioselective synthesis of four stereoisomers of lupinine and their derivatives.

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Section: Methodsmentioning

confidence: 99%

Double Ring‐Closing Metathesis Reaction of Nitrogen‐Containing Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives

2004

Chemistry A European J

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“…The vinyl functionality is very important and useful in organic synthesis as well as in polymer and pharma industries. Aryl vinyl/styrenyl ethers have been explored as nucleophiles in cycloaddition reactions, ene and aldol‐type additions, cyclopropanations and metathesis reactions and are commonly used as acyl anion equivalents . They have been effectively explored in the synthesis of polymers as well .…”

Section: Figurementioning

confidence: 99%

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

2018

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A one‐pot transition‐metal‐free synthesis of styrenyl ethers starting from 2‐aryloxy/alkoxy acetophenones is described. The protocol explores the use of tosyl hydrazide and potassium carbonate as a mild base via Bamford‐Stevens reaction to synthesize the styrenyl ethers. The protocol is very simple, practical and uses mild reaction conditions with simple reaction set‐up. This practical protocol proved to be scalable on gram quantity.

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“…N‐ (1‐Alkenyl)azoles 1 and 1‐alkenyl aryl ethers 2 (Scheme ) are important classes of building blocks in organic synthesis as well as synthetic targets throughout the polymer and life science industries. Indeed, vinyl aryl ethers constitute useful intermediates in a wide range of reactions (for example, cycloaddition,1 cyclopropanation,2 or metathesis reactions3) and they find applications in the synthesis of natural product analogues,4 biologically active molecules,5 and polymers 6 . N‐ vinylazoles have also been widely used in the preparation of structural templates.…”

Section: Introductionmentioning

confidence: 99%

Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

Taillefer¹,

Ouali²,

Renard³

et al. 2006

Chemistry A European J

122

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An efficient and straightforward copper-catalyzed method allowing vinylation of N- or O-nucleophiles with di- or trisubstituted vinyl bromides is reported. The procedure is applicable to a broad range of substrates since N-vinylation of mono-, di-, and triazoles as well as O-vinylation of phenol derivatives can be performed with catalytic amounts of copper iodide and inexpensive nitrogen ligands 3 or 8. In the case of more hindered vinyl bromides, the use of the original bidentate chelator 8 was shown to be more efficient to promote the coupling reactions than our key tetradentate ligand 3. The corresponding N-(1-alkenyl)azoles and alkenyl aryl ethers are obtained in high yields and selectivities under very mild temperature conditions (35-110 degrees C for N-vinylation reactions and 50-80 degrees C for O-vinylation reactions). Moreover, to our knowledge, this method is the first example of a copper-catalyzed vinylation of various azoles. Finally, this protocol, practical on a laboratory scale and easily adaptable to an industrial scale, is very competitive compared to the existing methods that allow the synthesis of such compounds.

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Stereocontrolled Preparation of a Nonpeptidal (−)-Spirobicyclic NK-1 Receptor Antagonist

Cited by 32 publications

References 14 publications

Double Ring‐Closing Metathesis Reaction of Nitrogen‐Containing Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives

Double Ring‐Closing Metathesis Reaction of Nitrogen‐Containing Tetraenes: Efficient Construction of Bicyclic Alkaloid Skeletons and Synthetic Application to Four Stereoisomers of Lupinine and Their Derivatives

A One Pot Transition‐Metal‐Free Synthesis of Styrenyl Ethers from 2‐Aryloxy/Alkoxy Acetophenones

Mild Copper‐Catalyzed Vinylation Reactions of Azoles and Phenols with Vinyl Bromides

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