Regioselective addition of 1-trimethylsilyloxy-1-methoxy-1,3-dienes to aldonitrones catalysed by trimethylsilyl triflate

Camiletti, Chiara; Dhavale, Dilip D.; Donati, Francesca Pucci; Trombini, Claudio

doi:10.1016/0040-4039(95)01468-w

Cited by 29 publications

(6 citation statements)

References 9 publications

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“…68 The scope of this process also included reactions with 1-trimethyl- siloxy-1,3-dienes 30, which generated g-adducts 31 in a regioselective manner (Scheme 13, Table 3). 69 3…”

Section: Scheme 12mentioning

confidence: 99%

Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones

Merino¹,

Tejero²

2011

Synlett

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Mannich-type reactions with nitrones, oximes, and hydrazones provide efficient approaches to b-amino carbonyl derivatives with nitrogen functionality existing in an intermediate oxidation state, as in the cases of hydroxylamine and hydrazine derivatives. By employing chiral substrates and catalysts enantiomerically pure substances can be prepared by using these processes. 1 Introduction 2 Mannich-Type Reactions with Nitrones 2.1 Metal Enolates 2.2 Silyl Ketene Acetals 3 Mannich-Type Reactions with Oximes 4 Mannich-Type Reactions with Hydrazones 5 Concluding Remarks

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“…68 The scope of this process also included reactions with 1-trimethyl- siloxy-1,3-dienes 30, which generated g-adducts 31 in a regioselective manner (Scheme 13, Table 3). 69 3…”

Section: Scheme 12mentioning

confidence: 99%

Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones

Merino¹,

Tejero²

2011

Synlett

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“…The utility of nitrone compounds as Mannich-type acceptors in vinylogous additions to cyclic and acyclic enoxy silanes was largely experienced by Trombini in the mid-1990s. , As shown in Scheme , the assemblage of racemic fagomine ( 256 ) 168 was ensured by the TMSOTf-catalyzed addition of nitrone 253 to d 4 -donor silyloxy furan 136 . In the event, erythro -configured butenolide 254 initially formed ( erythro/threo 6:4), which was then exposed to TBAF to afford bicyclic furanone 255 .…”

Section: Additions To Imines Nitrones and Iminium Ions (Mannich-type ...mentioning

confidence: 99%

The Vinylogous Aldol Reaction: A Valuable, Yet Understated Carbon−Carbon Bond-Forming Maneuver

et al. 2000

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“…1-Methoxy-1-siloxy-1,3-dienes display an intermediate reactivity and add to nitrones in 2 hours at -20°C in good to excellent yields in the presence of a catalytic amount of TMSOTf 48. Alkyl substitution on the 1,3-diene moiety does affect the regiochemistry of this reaction.…”

mentioning

confidence: 95%

Nucleophilic Additions to Nitrones

2000

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In recent years increasing interest has been devoted to widen the scope of the formerly studied reaction of nitrones with Grignard reagents to different nucleophilic compounds, including allylic organometallic compounds, sulfur stabilised anions, acetylides, lithiated heteroaromatic compounds etc. In addition, silylated nucleophiles are now routinely used under Mukaiyama conditions to give useful mild approaches to functionalized isoxazolidines. Attention has been also paid to the development of stereocontrolled processes; nitrones derived from glyceraldehyde and congeners have been carefully studied and interesting reversions of facial selectivity have been reported by complexing them with Lewis acids. N-Glycosyl nitrones are used to synthesise enantiomerically enriched amines after cleavage of the auxiliary group and reduction of the N-O bond. Very few attempts have been reported on reactions based on chiral catalysts. So far asymmetric catalysis has not found proper applications and the opportunities offered by nitrones will represent a major challenge in this field.

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Regioselective addition of 1-trimethylsilyloxy-1-methoxy-1,3-dienes to aldonitrones catalysed by trimethylsilyl triflate

Cited by 29 publications

References 9 publications

Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones

Mannich-Type Reactions of Nitrones, Oximes, and Hydrazones

The Vinylogous Aldol Reaction: A Valuable, Yet Understated Carbon−Carbon Bond-Forming Maneuver

Nucleophilic Additions to Nitrones

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