Reactivity of tert-butanesulfinamides in palladium-catalyzed allylic substitutions

Mistico, Laetitia; Ay, Emel; Huynh, Vaizanne; Bourderioux, Aurélie; Chemla, Fabrice; Ferreira, Franck; Oble, Julie; Pérez‐Luna, Alejandro; Poli, Giovanni; Prestat, Guillaume

doi:10.1016/j.jorganchem.2013.11.026

Cited by 15 publications

(13 citation statements)

References 27 publications

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“…In 2013, Prestat and co-workers reported a study on the Pd(0)-catalyzed allylic carbonates substitution reaction with tertbutanesulfinamides as chiral nitrogen nucleophiles to prepare enantiopure allylic sulfinamides. 48 Prior to this, Yudin's group…”

Section: Reaction With Olefinsmentioning

confidence: 99%

Syntheses and Transformations of Sulfinamides

Zhang¹,

Xi²,

He³

et al. 2021

Synthesis

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Sulfinamides, especially enantiopure sulfinamides, are widely used in organic and medicinal synthesis. Syntheses and transformations of racemic and enantioenriched sulfinamides have achieved great progress. Especially sulfinamides demonstrate interesting and valuable reactivity, which deserves to be concerned. This review summarizes the latest development in the synthesis and transformation of sulfinamides and will be helpful for future related research.

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Section: Reaction With Olefinsmentioning

confidence: 99%

Syntheses and Transformations of Sulfinamides

Zhang¹,

Xi²,

He³

et al. 2021

Synthesis

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“…Moreover, the stereoretention of the S center guaranteed the recovery of the products 33 in an enantiomerically pure form (Scheme 11). 17…”

Section: Scheme 9 Allylation Of Electron-deficient Arenesmentioning

confidence: 99%

π-Allylpalladium Complexes in Synthesis: An Update

Parisotto¹,

Deagostino²

2019

Synthesis

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This review aims to summarize the development of the chemistry of π-allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates.1 Introduction2 π-Allylpalladium Complexes Generated from Allyl Electrophiles2.1 Activated Allylic Compounds2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons2.3 Total Syntheses3 π-Allylpalladium Complexes Generated from Dienes3.1 Conjugated Dienes3.2 Allenes4 π-Allylpalladium Complexes Exploited as Reactants and Precatalysts4.1 Allylpalladium-Catalyzed Dehydrogenation4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters4.3 Allylpalladium-Based Precatalysts5 Conclusions

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“…Lithium or potassium anions of tert-butanesulfinamide (1) have been reported to react with carboxylic anhydrides [41] and esters [42,43] to provide the corresponding N-tert-butanesulfinyl amides, and with isocyanates [44] and 1,1'-carbonyldiimidazole [45] to give N-tert-butanesulfinyl ureas. Even though it has been an issue in certain cases, [41] these reactions have been usually carried groups in the presence of either tBuOK, as for the formation of 8, or NaH.…”

Section: N-acylation Of Tert-butanesulfinamidesmentioning

confidence: 99%

“…[65] This reaction has been recently reinvestigated by us using Pd(OAc) 2 /diphenylphosphino-ethane (dppe) as catalytic system in order to gain insight on the influence of N-substitution. [43] Unlike metallated tert-butanesulfinamide 1, anions of N-benzyl tert-butanesulfinamide and Nacetyl tert-butanesulfinamide (64) were found to react readily with allyl acetate. In the presence of BSA (N,O-bis(trimethyl) acetamide) and a catalytic amount of AcOK, the use of a strong base could be avoided and N-allylation of 1 to afford 63 was achieved in reasonable yield, despite competitive diallylation (Scheme 14).…”

Section: Mitsunobu Cyclizations Of Tertbutanesulfinamidesmentioning

confidence: 99%

tert-Butanesulfinamides as Nitrogen Nucleophiles in Carbon–Nitrogen Bond Forming Reactions

Hernandez

Chemla

Ferreira

et al. 2016

Chimia

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The use of tert-butanesulfinamides as nitrogen nucleophiles in carbon-nitrogen bond forming reactions is reviewed. This field has grown in the shadow of the general interest in N-tert-butanesulfinyl imines for asymmetric synthesis and occupies now an important place in its own right in the chemistry of the chiral amine reagent tert-butanesulfinamide. This article provides an overview of the area and emphasizes recent contributions wherein the tert-butanesulfinamides act as chiral auxiliaries or perform as nitrogen donors in metal-catalyzed amination reactions.

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Reactivity of tert-butanesulfinamides in palladium-catalyzed allylic substitutions

Cited by 15 publications

References 27 publications

Syntheses and Transformations of Sulfinamides

Syntheses and Transformations of Sulfinamides

π-Allylpalladium Complexes in Synthesis: An Update

tert-Butanesulfinamides as Nitrogen Nucleophiles in Carbon–Nitrogen Bond Forming Reactions

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