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2 article(s) from Montchamp, Jean-Luc

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

Karen R. Winters and
Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

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Graphical Abstract

Figure 1: Chiral phosphorus acids (CPAs) derived from BINOL, VAPOL, and SPINOL. R = H, Ph, 4-PhC₆H₄-, 4-β-nap...

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Scheme 1: The thiolic/thionic tautomeric equilibrium in thiophosphorus acids.

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Figure 2: Project strategy and requirements for C₁-symmetrical CPAs.

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Figure 3: BINOL CPA and C₁-symmetrical CPA targets 1–4.

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Scheme 2: Synthesis of tryptophol-derived thiophosphorus acid 1.

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Scheme 3: Synthesis of indole-derived thiophosphorus acid 2.

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Scheme 4: Synthesis of N-biphenyl-DOPO CPA 4.

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Scheme 5: Transfer hydrogenation of 2-phenylquinoline and transition-state proposed by Guinchard and coworker...

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Full Research Paper

Published 17 Oct 2022

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Phosphinate-containing heterocycles: A mini-review

Olivier Berger and
Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

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Scheme 1: McCormack synthesis.

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Scheme 2: Ring-closing metathesis.

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Scheme 3: Phospha-Dieckmann condensation.

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Scheme 4: Palladium-catalyzed oxidative arylation.

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Scheme 5: Tandem cross-coupling/Dieckmann condensation.

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Scheme 6: Rhodium-catalyzed double [2 + 2 + 2] cycloaddition.

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Scheme 7: Silver oxide-mediated alkyne–arene annulation.

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Scheme 8: Silver acetate-mediated alkyne–arene annulation.

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Scheme 9: Cyclization through phosphinylation/alkylation of malonate anion.

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Scheme 10: Tandem hydrophosphinylation/Michael/Michael reaction of allenyl-H-phosphinates.

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Scheme 11: 5-Membered “cyclo-PALA” via intramolecular Mitsunobu reaction.

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Scheme 12: 6-Membered “cyclo-PALA” via intramolecular Mitsunobu reaction.

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Scheme 13: Intramolecular Kabachnik–Fields reaction.

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Scheme 14: Tandem Kabachnik–Fields/alkylation reaction.

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Scheme 15: Tandem Kabacknik–Fields/C–N cross-coupling reaction.

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Scheme 16: Tandem Kabacknik–Fields/C-P cross-coupling reaction.

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Scheme 17: Heterocyclization via amide formation.

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Scheme 18: Cyclization via reductive amination.

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Scheme 19: H-Phosphinate alkylation.

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Scheme 20: Cyclization through intramolecular Michael addition.

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Scheme 21: Double Arbuzov reaction of bis(trimethylsiloxy)phosphine.

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Scheme 22: Diastereoselective ring-closing metathesis.

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Scheme 23: 2-Ketophosphonate/benzene annulation.

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Scheme 24: Tandem Kabachnik–Fields/transesterification reaction.

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Scheme 25: Tandem Kabachnik–Fields/transesterification reaction with oxazolidine.

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Review

Published 27 Mar 2014

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