Diastereospecific Synthesis of Enantiomerically Pure Polysubstituted Azetidines from 1,3-Amino Alcohols with Three Chiral Centers

Barluenga, José; Fernández-Marí, Félix; Viado, Argimiro L.; Aguilar, Enrique; Olano, Bernardo

doi:10.1021/jo960494b

Cited by 45 publications

(14 citation statements)

References 25 publications

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“…It was subsequently reported that diastereoselective cyclizations of the mesylates lead to similar results (Scheme 3.3) [21]. A modification of this method has been investigated.…”

Section: Formation Of a Càn Bondmentioning

confidence: 95%

Four‐Membered Heterocycles: Structure and Reactivity

Rousseau

Robin

2011

Modern Heterocyclic Chemistry

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“…It was subsequently reported that diastereoselective cyclizations of the mesylates lead to similar results (Scheme 3.3) [21]. A modification of this method has been investigated.…”

Section: Formation Of a Càn Bondmentioning

confidence: 95%

Four‐Membered Heterocycles: Structure and Reactivity

Rousseau

Robin

2011

Modern Heterocyclic Chemistry

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“…Compound (R,R)-4b was obtained as a colourless oil after purification 13 C NMR (100 MHz, CDCl 3 ): δ ϭ 2 ϫ 14.1 (2 ϫ CH 3 ), 22.6,23.0,26.8,28.5,29.5,29.9,31.9 (CH 2 (7), 228 (5), 220 (20), 114 (100), 91 (17). C 20 H 35 NO (305.50): calcd.…”

Section: (3r4r)-(؉)-3-(benzyloxymethyl)octan-4-amine [(Rr)-4b]mentioning

confidence: 99%

“…[16] One of the most reliable ways for the asymmetric synthesis of substituted azetidines remains the synthesis of a straight chain precursor, such as 3-amino-1-alkanols, with established stereochemistry and subsequent ring closure by intramolecular N-alkylation. [17] The synthesis of enantiomerically enriched 3-amino-1-alkanols has recently received much attention, as the direct catalytic asymmetric Mannich reaction was reported as a promising new method for their synthesis. The use of organometallic and amine catalysts in this reaction has recently been reviewed.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of 2‐Mono‐ and 2,3‐trans‐Disubstituted Azetidines

2004

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A versatile and efficient asymmetric synthesis of 2-monoand 2,3-trans-disubstituted azetidines with excellent diastereomeric (de = 93 to Ն 96%) and enantiomeric excesses (ee Ն 96%) in good overall yields is described. Virtually stereoisomerically pure differently N,O-protected 3-amino-1-alkanols were prepared as intermediates. Key steps are a diastereoselective α-alkylation of aldehyde SAMP-hydrazones with benzyloxymethyl chloride as the electrophile, and a nucleophilic 1,2-addition of various organocerium reagents to

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“…Other report showed the synthesis of (2R,4S)-3-methyl-2,4-diphenylazetidine by the reaction of (2S,3S)-3-amino-2-methyl-1,3-diphenylpropan-1-ol with Et 3 N and MsCl in basic medium 4 .Additionaly, a study shown the synthesis of trans-l-(Diphenylmethyl)-2-methyl-3-azetidinol by the reaction of threo-3-bromo-1,2-epoxybutane with diphenylmethylamine 5 . Also other report indicate the preparation of 2-[22 -{42 2 -substituted aryl-32 2 -chloro-22 2 -oxo-azetidine}-acetyl amino]-4-phenyl-1,3-thiazole by the reaction of 2-(22 -Arylidene-hydrazino-acetyl)-amino-4-phenyl-1,3-thiazole with chloroacetyl chloride in presence of triethylamine 6 .…”

mentioning

confidence: 99%

Design and synthesis of two azetidin-haloperidol derivatives using some strategies

Figueroa‐Valverde

Díaz-Cedillo²,

Elodia

et al. 2014

Orient. J. Chem

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In this study is reported a straight forward route for synthesis of two azetidin-haloperidol derivatives using some strategies. The first stage was achieved by the synthesis of an azetidine derivative (3) by the reaction of a haloperidol derivative (1) with chloroacetyl chloride in presence oftriethylamine. The second stage was achieved by reaction of an estradiol derivative with 1 to forma haloperidol-estradiol derivative (5) using boric acid as catalyst. Finally, the third stage involves the synthesis of a second azetidine-derivative (6) by the reaction of 5 with chloroacetyl chloride usingtriethylamine as catalyst. The structure of the compounds obtained was confirmed by elemental analysis, spectroscopy and spectrometry data. The proposed method offers some advantages such as simple procedure, low cost, and ease of workup.Key words: Azetidin-haloperidol derivatives, Elemental analysis, Spectroscopy. of 1,2,4-trisubstituted azetidines by reductive cyclization of aza-Michael adducts of chalcones 1 . Other study 2 showed the preparation of N-Benzyl-3-hydroxyazetidine by the reaction of N-Benzyl-3-chloro-2-hydroxypropylamine with NaHCO 3 in MeCN.

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Diastereospecific Synthesis of Enantiomerically Pure Polysubstituted Azetidines from 1,3-Amino Alcohols with Three Chiral Centers

Cited by 45 publications

References 25 publications

Four‐Membered Heterocycles: Structure and Reactivity

Four‐Membered Heterocycles: Structure and Reactivity

Asymmetric Synthesis of 2‐Mono‐ and 2,3‐trans‐Disubstituted Azetidines

Design and synthesis of two azetidin-haloperidol derivatives using some strategies

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