Asymmetric nitrone cycloadditions and their application to the synthesis of enantiopure pyrrolidine and pyrrolizidine derivatives

Argyropoulos, N. G.; Panagiotidis, Theodoros; Coutouli‐Argyropoulou, Evdoxia; Raptopoulou, Catherine P.

doi:10.1016/j.tet.2006.10.076

Cited by 23 publications

(9 citation statements)

References 55 publications

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“…After extraction with DCM (5 × 300 mL), the organic layers were dried and concentrated. A purification by silica gel chromatography (Et 2 …”

Section: (7s7as)-7-(tert-butyldimethylsilyloxy)pyrrolizidin-3-one (3)mentioning

confidence: 99%

“…One commonly encountered function of this skeleton is in the formation of rigid dipeptide mimics. 1 Moreover, these bicyclic systems are known to be effective intermediates in the preparation of alkaloids such as the polyhydroxylated pyrrolizidines or indolizidines, [2][3][4] and of more complex structures like lepadiformine 5 or furopyrrolizidinone. 6 The synthesis of pyrrolizidin-3-ones mono-or disubstituted at positions 1 or 7 was reviewed in 2000.…”

Section: Introductionmentioning

confidence: 99%

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Asymmetric syntheses of functionalized pyrrolizidin-3-ones

Greck

Thomassigny²,

Bouc

2012

Arkivoc

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“…After extraction with DCM (5 × 300 mL), the organic layers were dried and concentrated. A purification by silica gel chromatography (Et 2 …”

Section: (7s7as)-7-(tert-butyldimethylsilyloxy)pyrrolizidin-3-one (3)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Asymmetric syntheses of functionalized pyrrolizidin-3-ones

Greck

Thomassigny²,

Bouc

2012

Arkivoc

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“…144 The cycloadditions proceeded with complete regioselectivity to yield a 2:1 mixture of diastereomers (the cycloaddition of one of the enantiomeric nitrones is depicted in Scheme 44).…”

Section: Figure 23mentioning

confidence: 99%

Asymmetric 1,3-dipolar cycloadditions of acrylamides

2010

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This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references)

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“…Following model studies by Goti, Brandi, and co-workers 143 , Wightman 144 , and others 145 , the cycloaddition approach has been used extensively for the synthesis of pyrrolizidine alkaloids such as lentiginosine, 146 alexines, 147 and related pyrrolizidine alkaloids. 148 from tri-O-benzyl-D-arabinofuranose, reacts stereoselectively with allyl alcohol to give the bicyclic adducts 119 and 120 resulting from exo-anti and endo-anti cycloaddition modes, in a ratio of $4:1 (Scheme 97). The major isomer was converted in three steps into 7-deoxycasuarin 121.…”

Section: Cycloaddition To Cyclic Nitronesmentioning

confidence: 99%