A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

Aubineau, Thomas; Cossy, Janine

doi:10.1021/acs.orglett.8b03141

Cited by 22 publications

(14 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A recent method for morpholine substituted derivatives was developed by Cossy's group . Their approach involves the reaction between readily available oxiranes and amino alcohols, via a Pd‐catalyzed Tsuji‐Trost reaction, using Pd(0) as a catalyst (Scheme ).…”

Section: Synthesis Of Morpholinesmentioning

confidence: 99%

“… A Pd‐catalyzed reaction of oxiranes and amino‐alcohols. Reagents and conditions : a) Pd(PPh 3 ) 4 (1 mol %), DCM, rt, 12 h; b) FeCl 3 ⋅ 6H 2 O (20 mol %), 50 °C, 4 h; c) Mg (10 equiv), MeOH, THF, 2 h (overall yield: 42–93 %) …”

Section: Synthesis Of Morpholinesmentioning

confidence: 99%

“…A recent method for morpholine substituted derivatives was developed by Cossy's group. [69] Their approach involves the reaction between readily available oxiranes and amino alcohols, via a Pd-catalyzed Tsuji-Trost reaction, using Pd(0) as a catalyst (Scheme 18). The formed cis/trans mixture is thermodynamically pushed toward the cis product, by addition of FeCl 3 which causes a sequence of ring opening and closure.…”

Section: Scheme 13 a Nbs-mediated Multicomponent Reaction For Morphomentioning

confidence: 99%

“…[66] (TMSCN: trimethylsilyl cyanide, PG: protecting group). [69] as well as diastereoselectivity (up to 21 : 1) between the major and minor annulation products, while it was applicable for gram scale-up.…”

Section: Scheme 13 a Nbs-mediated Multicomponent Reaction For Morphomentioning

confidence: 99%

See 3 more Smart Citations

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

2020

View full text Add to dashboard Cite

Morpholine is a frequently used heterocycle in medicinal chemistry and a privileged structural component of bioactive molecules. This is mainly due to its contribution to a plethora of biological activities as well as to an improved pharmacokinetic profile of such bioactive molecules. The synthesis of morpholines is a subject of much study due to their biological and pharmacological importance, with the last such review being published in 2013. Here, an overview of the main approaches toward morpholine synthesis or functionalization is presented, emphasizing on novel work which has not been reviewed so far. This review is an update on synthetic strategies leading to easily accessible libraries of bioactives which are of interest for drug discovery projects.

show abstract

Section: Synthesis Of Morpholinesmentioning

confidence: 99%

Section: Synthesis Of Morpholinesmentioning

confidence: 99%

Section: Scheme 13 a Nbs-mediated Multicomponent Reaction For Morphomentioning

confidence: 99%

Section: Scheme 13 a Nbs-mediated Multicomponent Reaction For Morphomentioning

confidence: 99%

See 2 more Smart Citations

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

2020

View full text Add to dashboard Cite

show abstract

“…For our part, we reported a one‐pot sequential Pd/Fe catalysis to access polysubstituted morpholines, starting from amino‐alcohols 99 and vinyl epoxides 98 (Scheme ) . Under palladium(0) catalysis, a π‐allylic complex 101 is formed from the vinyl epoxide 98 .…”

Section: Cyclization Through Sequential Bond Formationmentioning

confidence: 99%

Metal‐Catalyzed Cyclization: Synthesis of (Benzo)morpholines and (Benzo)[1,4]dihydrooxazines

Aubineau

Cossy

2019

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

A review of the most recent metal-catalyzed cyclizations to access morpholines and their unsaturated derivatives, from 1993 to 2019, is reported. The review is organized accord-[a] Molecular, 7513ing to the bond(s) formed during the process. Special importance has been given to the mechanistic details of the reactions.[a] Conditions A: (MeCN) 2 PdCl 2 (10 mol-%), CH 2 Cl 2 , r.t., 5 h; Conditions B: TfOH (10 mol-%), CH 2 Cl 2 , -20°C, 5 h.

show abstract

Catalyst‐ and Base‐free One‐pot, Multicomponent, De Novo Assembly of Structurally Diverse Morpholine Glycoconjugates

Khanam

Lal

Mandal

2022

Chemistry An Asian Journal

View full text Add to dashboard Cite

A catalyst-, metal-and base-free unprecedented one-pot multicomponent synthetic strategy has been established for the construction of various substituted morpholine glycoconjugates through four-component reactions of glycosyl amino alcohol, chloroacetone, acid, and isocyanides. Unexpectedly, this one-pot approach generates only the cyclized morpholine scaffolds rather than normal Ugi adduct without any external base. This reaction proceeds via in situ formations of Schiff-base followed by an intramolecular halogen displacement process, finally the Joullie-Ugi reaction takes place leading to the corresponding products with a mixture of diastereomers.

show abstract

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

Cited by 22 publications

References 41 publications

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

Morpholine As a Scaffold in Medicinal Chemistry: An Update on Synthetic Strategies

Metal‐Catalyzed Cyclization: Synthesis of (Benzo)morpholines and (Benzo)[1,4]dihydrooxazines

Catalyst‐ and Base‐free One‐pot, Multicomponent, De Novo Assembly of Structurally Diverse Morpholine Glycoconjugates

Contact Info

Product

Resources

About