The Wittig-Horner Reaction in Heterogenous Media VIII<sup>1</sup>. Cyclisation During the Aldolisation Step from Aqueous Glutaraldehyde

Villiéras, J.; Rambaud, M.; Graff, M.

doi:10.1080/00397918608057702

Cited by 26 publications

(10 citation statements)

References 3 publications

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“…The following cinnamyl azides were prepared through known procedures and have been previously characterized: 1a , , 1c – 1d , , 1e – 1f , , 1g , , 1h , , 1j – 1k , , 1o , , 1p – 1q , 1t , ,, 1u – 1v , 1w , − and 1hh . , …”

Section: Methodsmentioning

confidence: 99%

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

2020

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Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon atoms attached to a nitrogen atom.Over 30 examples are provided with an average isolated yield of 71% (ranging from 40% to 94%). The reaction was easily scaled to use more than one gram of starting material, and the products can be readily diversified.

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Section: Methodsmentioning

confidence: 99%

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

2020

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“…83 a domino sequence of Wittig and aldol on dialdehyde. 85 In fact it has been method of choice for quick access to cyclic MBH adduct and its application. 86…”

Section: Cycloaddition Approachesmentioning

confidence: 99%

Intramolecular Morita–Baylis–Hillman and Rauhut–Currier reactions. A catalytic and atom economic route for carbocycles and heterocycles

Bharadwaj

2015

RSC Adv.

119

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“…Dihydrocodeinone (19) had earlier been converted to codeine (2) [11]. Thus, Dwight W. Weller and Henry Rapoport found that ketalization of dihydrocodeinone (19) with trimethylorthoformate in methanol with a trace of sulfuric acid followed by toluenesulfonic acid (in chloroform) resulted in the elimination of methanol and yielded the corresponding enol ether (20) in 82% yield (for the two steps). The hydrobromide of the enol ether (prepared from the enol ether with aqueous HBr) on treatment with Nbromoacetamide in methanol produced the corresponding bromodihydrocodeine dimethyl ketal (21) in 83% yield and treatment of the latter with potassium tert-butoxide at 60 o C in dimethyl sulfoxide for 7 hours resulted in an 87% yield of the ketal of codeinone itself; Fig.…”

Section: : Kathlyn a Parker And Demosthenes Fokas [8]mentioning

confidence: 99%

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

Mascavage¹,

Wilson²,

Dalton³

2006

COS

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Morphine (1) and its O-methylated analogue codeine (2), analgesic alkaloids of the opium poppy (Papaver Somniferium), have been targets of organic chemists engaged in synthetic activities for at least half a century. The "first" (Gates) and "most efficient" (Rice) syntheses of morphine (1) and codeine (2) are well known and have been reviewed and analyzed extensively numerous times. However, syntheses of the same two alkaloids that have been reported since 1992 and which have been used as devices to advance the art of organic synthesis are not as widely recognized and they have not been as thoroughly reviewed. Here they are analyzed in the spirit of the use of these two compounds as templates. Further, since both racemic and enantiospecific syntheses are important and since all eight (8) approaches (since 1992) are sufficiently different so as to warrant more tha n superficial examination, they are all considered.

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The Wittig-Horner Reaction in Heterogenous Media VIII¹. Cyclisation During the Aldolisation Step from Aqueous Glutaraldehyde

Cited by 26 publications

References 3 publications

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

Intramolecular Morita–Baylis–Hillman and Rauhut–Currier reactions. A catalytic and atom economic route for carbocycles and heterocycles

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

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The Wittig-Horner Reaction in Heterogenous Media VIII1. Cyclisation During the Aldolisation Step from Aqueous Glutaraldehyde

Cited by 26 publications

References 3 publications

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles

Intramolecular Morita–Baylis–Hillman and Rauhut–Currier reactions. A catalytic and atom economic route for carbocycles and heterocycles

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

Contact Info

Product

Resources

About

The Wittig-Horner Reaction in Heterogenous Media VIII¹. Cyclisation During the Aldolisation Step from Aqueous Glutaraldehyde