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5 article(s) from Delaude, Lionel

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

Nedra Touj,
François Mazars,
Guillermo Zaragoza and
Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

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Figure 1: Various types of stable singlet carbenes and their acronyms.

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Figure 2: Various types of NHC·CS₂ zwitterions and their coordination modes.

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Scheme 1: Synthesis of CAAC·CS₂ zwitterion 2 from its free carbene parent 1.

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Scheme 2: Synthesis of CAAC·CS₂ zwitterions 4a–c with KN(SiMe₃)₂.

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Scheme 3: Synthesis of 1,2,3-triazolium iodides 5a–f.

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Scheme 4: Synthesis of MIC·CS₂ zwitterions 6a and 6b with KN(SiMe₃)₂.

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Scheme 5: Synthesis of MIC·CS₂ zwitterions 6c–f with NaOt-Bu.

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Figure 3: ORTEP representations of zwitterions 4a (CAAC-Mes-Cy·CS₂, top) and 4c (CAAC-Die-MePh·CS₂, bottom) w...

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Figure 4: ORTEP representations of zwitterions 6b (MIC-Dip-Ph-Me·CS₂, top) and 6e (MIC-Mes-Bu-Me·CS₂, bottom)...

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Published 20 Dec 2023

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Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

Valerian Dragutan,
Ileana Dragutan,
Albert Demonceau and
Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

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Scheme 1: Intramolecular (A) and intermolecular (B) enyne metathesis reactions.

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Scheme 2: Ene–yne and yne–ene mechanisms for intramolecular enyne metathesis reactions.

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Scheme 3: Metallacarbene mechanism in intermolecular enyne metathesis.

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Scheme 4: The Oguri strategy for accessing artemisinin analogs 1a–c through enyne metathesis.

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Scheme 5: Access to the tetracyclic core of nanolobatolide (2) via tandem enyne metathesis followed by an Eu(...

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Scheme 6: Synthesis of (−)-amphidinolide E (3) using an intermolecular enyne metathesis as the key step.

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Scheme 7: Synthesis of amphidinolide K (4) by an enyne metathesis route.

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Scheme 8: Trost synthesis of des-epoxy-amphidinolide N (5) [72].

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Scheme 9: Enyne metathesis between the propargylic derivative and the allylic alcohol in the synthesis of the...

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Scheme 10: Synthetic route to amphidinolide N (6a).

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Scheme 11: Synthesis of the stereoisomeric precursors of amphidinolide V (7a and 7b) through alkyne ring-closi...

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Scheme 12: Synthesis of the anthramycin precursor 8 from ʟ-methionine by a tandem enyne metathesis–cross metat...

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Scheme 13: Synthesis of (−)‐clavukerin A (9) and (−)‐isoclavukerin A (10) by an enyne metathesis route startin...

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Scheme 14: Synthesis of (−)-isoguaiene (11) through an enyne metathesis as the key step.

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Scheme 15: Synthesis of erogorgiaene (12) by a tandem enyne metathesis/cross metathesis sequence using the sec...

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Scheme 16: Synthesis of (−)-galanthamine (13) from isovanilin by an enyne metathesis.

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Scheme 17: Application of enyne metathesis for the synthesis of kempene diterpenes 14a–c.

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Scheme 18: Synthesis of the alkaloid (+)-lycoflexine (15) through enyne metathesis.

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Scheme 19: Synthesis of the AB subunits of manzamine A (16a) and E (16b) by enyne metathesis.

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Scheme 20: Jung's synthesis of rhodexin A (17) by enyne metathesis/cross metathesis reactions.

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Scheme 21: Total synthesis of (−)-flueggine A (18) and (+)-virosaine B (19) from Weinreb amide by enyne metath...

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Scheme 22: Access to virgidivarine (20) and virgiboidine (21) by an enyne metathesis route.

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Scheme 23: Enyne metathesis approach to (−)-zenkequinone B (22).

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Scheme 24: Access to C-aryl glycoside 23 by an intermolecular enyne metathesis/Diels–Alder cycloaddition.

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Scheme 25: Synthesis of spiro-C-aryl glycoside 24 by a tandem intramolecular enyne metathesis/Diels–Alder reac...

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Scheme 26: Pathways to (−)-exiguolide (25) by Trost’s Ru-catalyzed enyne cross-coupling and cross-metathesis [94].

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Published 16 Apr 2020

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Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

Morgan Hans,
Jan Lorkowski,
Albert Demonceau and
Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

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Scheme 1: Various synthetic paths leading to the formation of NHCs.

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Scheme 2: Retrosynthetic path for the preparation of symmetrical imidazolium and imidazolinium salts from sim...

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Figure 1: Structures of the imidazolium and imidazolinium salts discussed in this study and their acronyms.

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Scheme 3: Synthesis of 1,3-dicyclohexylimidazolium tetrafluoroborate (ICy·HBF₄).

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Scheme 4: Synthesis of 1,3-dibenzylimidazolium tetrafluoroborate (IBn·HBF₄).

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Scheme 5: Synthesis of 1,3-dimesitylimidazolium salts (IMes·HCl and IMes·HBF₄).

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Scheme 6: Synthesis of 1,3-dimesitylimidazolinium chloride (SIMes·HCl).

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Scheme 7: Synthesis of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IDip·HCl).

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Scheme 8: Synthesis of 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (SIDip·HCl).

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Scheme 9: Synthesis of 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazolium chloride (IDip*·HCl).

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Published 25 Nov 2015

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Metathesis access to monocyclic iminocyclitol-based therapeutic agents

Ileana Dragutan,
Valerian Dragutan,
Carmen Mitan,
Hermanus C.M. Vosloo,
Lionel Delaude and
Albert Demonceau

Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81

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Scheme 1: Well-defined Mo- and Ru-alkylidene metathesis catalysts.

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Scheme 2: Representative pyrrolidine-based iminocyclitols.

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Scheme 3: Synthesis of (±)-(2R*,3R*,4S*)-2-hydroxymethylpyrrolidin-3,4-diol (18), (±)-2-hydroxymethylpyrrolid...

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Scheme 4: Synthesis of enantiopure iminocyclitol (−)-(2S,3R,4S,5S)-2,5-dihydroxymethylpyrrolidin-3,4-diol (23...

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Scheme 5: Synthesis of 1,4-dideoxy-1,4-imino-D-allitol (29) and formal synthesis of (2S,3R,4S)-3,4-dihydroxyp...

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Scheme 6: Synthesis of iminocyclitols 35 and 36.

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Scheme 7: Total synthesis of iminocyclitols 40 and 44.

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Scheme 8: Synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [(+)-DMDP] (49) and (−)-bulgecinine (50).

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Scheme 9: Synthesis of (+)-broussonetine G (53).

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Scheme 10: Structural features of broussonetines 54.

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Scheme 11: Synthesis of broussonetines by cross-metathesis.

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Scheme 12: Representative piperidine-based iminocyclitols.

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Scheme 13: Total synthesis of 1-deoxynojirimycin (62) and 1-deoxyaltronojirimycin (65).

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Scheme 14: Synthesis by RCM of 1-deoxymannonojirimycin (63) and 1-deoxyallonojirimycin (66).

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Scheme 15: Total synthesis of (+)-1-deoxynojirimycin (62).

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Scheme 16: Synthesis of ent-1,6-dideoxynojirimycin (83) and 5-amino-1,5,6-trideoxyaltrose (84).

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Scheme 17: Synthesis of 1-deoxygalactonojirimycin (64), 1-deoxygulonojirimycin (91) and 1-deoxyidonojirimycin (...

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Scheme 18: Synthesis of L-1-deoxyaltronojirimycin (96).

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Scheme 19: Synthesis of 1-deoxymannonojirimycin (63) and 1-deoxyaltronojirimycin (65).

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Scheme 20: Synthesis of 5-des(hydroxymethyl)-1-deoxymannonojirimycin (111) and 5-des(hydroxymethyl)-1-deoxynoj...

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Scheme 21: Synthesis of D-1-deoxygulonojirimycin (91) and L-1-deoxyallonojirimycin (122).

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Scheme 22: Total synthesis of fagomine (129), 3-epi-fagomine (126) and 3,4-di-epi-fagomine (130).

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Scheme 23: Total synthesis of (+)-adenophorine (135).

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Scheme 24: Total synthesis of (+)-5-deoxyadenophorine (138) and analogues 142–145.

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Scheme 25: Synthesis by RCM of 1,6-dideoxy-1,6-iminoheptitols 148 and 149.

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Scheme 26: Synthesis by RCM of oxazolidinyl azacycles 152 and 154.

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Scheme 27: Representative azepane-based iminocyclitols.

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Scheme 28: Synthesis of hydroxymethyl-1-(4-methylphenylsulfonyl)azepane 3,4,5-triol (169).

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Scheme 29: Synthesis by RCM of tetrahydropyridin-3-ol 171 and tetrahydroazepin-3-ol 173.

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Published 27 May 2011

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Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes

Yannick Borguet,
Xavier Sauvage,
Guillermo Zaragoza,
Albert Demonceau and
Lionel Delaude

Beilstein J. Org. Chem. 2010, 6, 1167–1173, doi:10.3762/bjoc.6.133

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Scheme 1: Reaction of homobimetallic ruthenium–indenylidene complex 1 with ethylene.

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Scheme 2: Schematic illustration of tandem assisted catalysis with complexes 1 and 2.

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Scheme 3: Tandem RCM/ATRC of 2,2,2-trichloro-N-(octa-1,7-dien-3-yl)acetamide (4) catalyzed by complex 1.

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Scheme 4: Ruthenium catalyzed transformation of substrate 16.

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Published 08 Dec 2010

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