α-Amido Sulfones as Stable Precursors of Reactive<i>N-</i>Acylimino Derivatives

Petrini, Marino

doi:10.1021/cr050528s

Cited by 236 publications

(118 citation statements)

References 190 publications

Supporting

Mentioning

116

Contrasting

Unclassified

Order By: Relevance

“…1,6,[9][10][11][12] Recently, we have described three independent, efficient methods for the synthesis of 1-(N-acylamino)alkyltriphenylphosphonium salts 4 (1 = 4 if Z = Ph 3 P + X -and X = Br, I or BF 4 ), including hitherto unknown 1-substituted-1-(Nacylamino)alkyltriphenylphosphonium salts (R 2 ≠ H). [13][14][15][16][17][18][19] We have also demonstrated that phosphonium salts 4 are effective and convenient amidoalkylating agents when activated with organic bases (DBU or i-Pr 2 EtN).…”

Section: Methodsmentioning

confidence: 99%

N-(1-acyloaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in α-amidoalkylation reactions

Październiok-Holewa¹,

Adámek²,

Zielińska³

et al. 2012

Arkivoc

View full text Add to dashboard Cite

Abstract1-(N-Acylamino)alkyltriphenylphosphonium salts 4, when treated with DBU, DBN or TBD in CD 3 CN or MeCN, were transformed immediately into the corresponding 1-(Nacylamino)alkylamidinium or guanidinium salts 5. Salts 5 with a proton at the α-position underwent slow transformation to the corresponding enamides 6. 1-(NAcylamino)alkyltriphenylphosphonium salts 4, amidinium or guanidinium salts 5, as well as enamides 6 reacted readily with β-dicarbonyl compounds in the presence of corresponding base under microwave irradiation at 60 o C to give the expected product of α-amidoalkylation of the enolate anion. The role of 1-(N-acylamino)alkylamidinium or guanidinium salts 5 as reactive intermediates in α-amidoalkylation with 1-(N-acylamino)alkyltriphenylphosphonium salts is discussed.

show abstract

Section: Methodsmentioning

confidence: 99%

N-(1-acyloaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in α-amidoalkylation reactions

Październiok-Holewa¹,

Adámek²,

Zielińska³

et al. 2012

Arkivoc

View full text Add to dashboard Cite

show abstract

“…In addition, heteroaromatic aldehyde-derived sulfones could also serve as substrates in 35 7 Sc(OTf) 3 57 8 Ga(OTf) 3 71 9 Cu(OTf) 2 Table 2, entries 12 and 13). Aliphatic aldehydes led to moderate to good yields of 2 (Table 2, entries [14][15][16][17][18][19]. For selected substrates, higher yields could be obtained using a catalyst loading of 5 mol% with 5 equiv.…”

Section: Bismuth Triflate-catalyzed Sakurai Allylation Reactionmentioning

confidence: 99%

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

Ollevier

2011

Bismuth-Mediated Organic Reactions

View full text Add to dashboard Cite

Bismuth triflate was found to be an efficient catalyst both in the Mannich-type reaction of silyl enolates and in the Sakurai reaction of allyltrimethylsilane with N-alkoxycarbonylamino sulfones. The reactions proceeded smoothly with a low catalyst loading of Bi(OTf)(3)·4H(2)O (0.5-5.0 mol%) to afford the corresponding protected β-amino carbonyl compounds and homoallylic amines in very good yields (up to 96%). The latter compounds could also be obtained via a bismuth-mediated three-component reaction. We have also developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in a low catalyst loading (1 mol%). The reaction proceeds rapidly and affords the corresponding 5-[hydroxy(aryl)methyl]furan-2(5H)-ones in high yields with good to very good diastereoselectivities (diastereoisomeric ratios>98:2). Such selectivities, although previously reported with other Lewis acids, could be achieved with a much lower catalyst loading. 5-[Hydroxy(alkyl)methyl]furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities. The vinylogous Mukaiyama aldol reaction has also been extended to 2,2-dimethyl-6-methylene-4-(trimethyl-silyloxy)-1,3-diox-4-ene using 1 mol% of Bi(OTf)(3)·4H(2)O.

show abstract

“…48 The chiral α-amido-sulfone 113 can be readily obtained by reaction of (S)-prolinal 112 with BocNH 2 and benzenesulfinic acid (Scheme 27). 49 Reaction of the α-amido-sulfone 113 under basic conditions initially produces the N-acylimine 114 that subsequently adds the nitromethane anion leading to the corresponding adduct, 115, with satisfactory diastereoselectivity.…”

Section: Scheme 26mentioning

confidence: 99%

Nitroalkanes as key building blocks for the synthesis of heterocyclic derivatives

Ballini¹,

Petrini²

2008

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

α-Amido Sulfones as Stable Precursors of ReactiveN-Acylimino Derivatives

Cited by 236 publications

References 190 publications

N-(1-acyloaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in α-amidoalkylation reactions

N-(1-acyloaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in α-amidoalkylation reactions

Bismuth-Catalyzed Addition of Silyl Nucleophiles to Carbonyl Compounds and Imines

Nitroalkanes as key building blocks for the synthesis of heterocyclic derivatives

Contact Info

Product

Resources

About