Sulfuranes. XVII. Reactions of secondary amides with a diaryldialkoxysulfurane. Selective method for the rapid cleavage of secondary amides

Martin, J. C.; Franz, James A.

doi:10.1021/ja00854a029

Cited by 29 publications

(17 citation statements)

References 5 publications

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“…This reagent is commercially available and can be prepared from diaryl sulfides, bromine, and potassium hexafluoro‐2‐phenyl‐2‐propoxide in mole scale . Martin and Franz have developed a general method for preparing S,S ‐diarylsulfilimines 9 in good yields by the mild reactions of these sulfuranes with amines, amides, and sulfonamides (Scheme ) …”

Section: Synthesis Of Sulfiliminesmentioning

confidence: 99%

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α‐Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity

Tian

Song

Hashmi

2020

Chemistry A European J

106

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Catalytic approaches to pharmaceutically important bioactive skeletons through gold carbene intermediates have experienced a dramatic development in the last decade. Although various carbene precursors continue to play an important role in heterocyclic syntheses, these reagents are associated with some drawbacks in terms of functional group tolerance, synthetic methods and safety limitations. A new generation of nitrene transfer reagents was established in 2019: the sulfilimines. These are safe, inexpensive and readily available. They can conveniently be stored and handled, and thus represent ideal reagents for the fast and modular modification of scaffolds and the preparation of libraries by intermolecular reactions of two components. Both the practical methods for synthesizing sulfilimines and the versatility of these ylidic species in gold‐catalyzed preparation of structural diversity, for both heterocycles and carbocycles, will be outlined in this Concept article.

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Section: Synthesis Of Sulfiliminesmentioning

confidence: 99%

“…[36] Martin and Franz have developedageneral methodfor preparing S,S-diarylsulfilimines 9 in good yields by the mild reactions of theses ulfuranes with amines,a mides, and sulfonamides (Scheme 5). [37] Direct NÀHfunctionalization of free NH-sulfilimines…”

Section: Reaction Of Diaryldialkoxysulfuranes With Amines or Amidesmentioning

confidence: 99%

α‐Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity

Tian

Song

Hashmi

2020

Chemistry A European J

106

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“…Although many classical methods exist for the hydrolysis of primary and tertiary amides, the efficient hydrolysis of sec-ondary amides has proven to be more problematic [9] and requires special conditions. Although many classical methods exist for the hydrolysis of primary and tertiary amides, the efficient hydrolysis of sec-ondary amides has proven to be more problematic [9] and requires special conditions.…”

Section: Resultsmentioning

confidence: 99%

“…We first focused on the non-conjugated derivatives. Although many classical methods exist for the hydrolysis of primary and tertiary amides, the efficient hydrolysis of sec-ondary amides has proven to be more problematic [9] and requires special conditions. The cleavage of secondary amides bonds requires harsh conditions, such as a strong acidic medium, [10] which is not compatible with sensitive functional groups.…”

Section: Resultsmentioning

confidence: 99%

A Route for the Total Synthesis of Enantiomerically Enriched Jasmonates 12‐COOH‐JA and 12‐COOH‐JA‐Ile

et al. 2014

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“…A thorough literature search led to a number of other possible amides32–35 as alternatives for what we had in mind (Scheme ). We first investigated the aniline amide (anilide) since the conditions reported by Martin and Franz32 for its cleavage were remarkably mild.…”

Section: The Second Assault At the Cp Moleculesmentioning

confidence: 99%

The CP Molecule Labyrinth: A Paradigm of How Endeavors in Total Synthesis Lead to Discoveries and Inventions in Organic Synthesis

Nicolaou¹,

Baran²

2002

Angew. Chem. Int. Ed.

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Imagine an artist carving a sculpture from a marble slab and finding gold nuggets in the process. This thought is not a far-fetched description of the work of a synthetic chemist pursuing the total synthesis of a natural product. At the end of the day, he or she will be judged by the artistry of the final work and the weight of the gold discovered in the process. However, as colorful as this description of total synthesis may be, it does not entirely capture the essence of the endeavor, for there is much more to be told, especially with regard to the contrast of frustrating failures and exhilarating moments of discovery. To fully appreciate the often Herculean nature of the task and the rewards that accompany it, one must sense the details of the enterprise behind the scenes. A more vivid description of total synthesis as a struggle against a tough opponent is perhaps appropriate to dramatize these elements of the experience. In this article we describe one such endeavor of total synthesis which, in addition to reaching the target molecule, resulted in a wealth of new synthetic strategies and technologies for chemical synthesis. The total synthesis of the CP molecules is compared to Theseus' most celebrated athlos (Greek for exploit, accomplishment): the conquest of the dreaded Minotaur, which he accomplished through brilliance, skill, and bravery having traversed the famous labyrinth with the help of Ariadne. This story from Greek mythology comes alive in modern synthetic expeditions toward natural products as exemplified by the total synthesis of the CP molecules which serve as a paradigm for modern total synthesis endeavors, where the objectives are discovery and invention in the broader sense of organic synthesis.

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Sulfuranes. XVII. Reactions of secondary amides with a diaryldialkoxysulfurane. Selective method for the rapid cleavage of secondary amides

Cited by 29 publications

References 5 publications

α‐Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity

α‐Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity

A Route for the Total Synthesis of Enantiomerically Enriched Jasmonates 12‐COOH‐JA and 12‐COOH‐JA‐Ile

The CP Molecule Labyrinth: A Paradigm of How Endeavors in Total Synthesis Lead to Discoveries and Inventions in Organic Synthesis

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