Samarium Diiodide-Induced Reductive Cross-Coupling of Nitrones with Aldehydes and Ketones

Masson, Géraldine; Py, Sandrine; Vallée, Yannick

doi:10.1002/1521-3773(20020517)41:10<1772::aid-anie1772>3.0.co;2-q

Cited by 127 publications

(62 citation statements)

References 36 publications

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“…15,16,22 While numerous reactions have been developed for SmI 2 , its scope in synthesis has certainly not been exhausted and new applications for this mild and selective single-electron-transfer reagent are steadily being discovered. 11,14,15,24,25 One of the unique features of SmI 2 is that the addition of cosolvents or additives can be used to control its reactions.…”

Section: Background and Introductionmentioning

confidence: 99%

Mechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions

Flowers¹

2008

Synlett

171

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This account describes work, performed by my research group during the past decade, designed to understand the mechanistic roles of cosolvents and additives in reductions involving samarium(II) iodide (SmI 2 ). Emphasis is placed on studies designed to elucidate the roles of the cosolvent hexamethylphosphoramide (HMPA) and proton donors (water, alcohols, and glycols) in the mechanisms of important bond-forming reactions and reductions initiated by SmI 2 .

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Section: Background and Introductionmentioning

confidence: 99%

Mechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions

Flowers¹

2008

Synlett

171

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“…Nitrones are able to undergo reductive samarium diiodide-induced coupling with both carbonyl derivatives [96] and α,β-unsaturated esters.…”

Section: Scheme 25mentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

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This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

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“…170 Samarium(II) iodide can also act as a radical trap (see Section 2.7.4) and, thus, permits irreversible addition to aldehydes and ketones; reduction of nitrone 420 to a ketyl-like radical is followed by chemoselective addition to the aldehyde of 421 (Scheme 130). 280 The methodology appears to be remarkably powerful, with no limitations in the structure of either substrate being observed. The reaction shows excellent chemoselectivity for aldehydes versus ketones.…”

Section: Radical Additions To C]x Bondsmentioning

confidence: 99%

Radicals in organic synthesis. Part 1

Rowlands

2009

Tetrahedron

205

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Samarium Diiodide-Induced Reductive Cross-Coupling of Nitrones with Aldehydes and Ketones

Cited by 127 publications

References 36 publications

Mechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions

Mechanistic Studies on the Roles of Cosolvents and Additives in Samarium(II)-Based Reductions

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Radicals in organic synthesis. Part 1

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