Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction

Andrei V. Malkov; Lanre Gouriou; Guy C. Lloyd-Jones; Ivo Stary; Vratislav Langer; Paul Spoor; Victoria Vinader; Pavel Kocovsky

doi:10.1002/chem.200501574

Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction

Andrei V. Malkov^*, Lanre Gouriou, Guy C. Lloyd-Jones, Ivo Stary, Vratislav Langer, Paul Spoor, Victoria Vinader, Pavel Kocovsky

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Application of new chiral ligands (R)-(-)-12a and (S)-(+)-12c (VALDY), derived from amino acids, to the title reaction, involving cinnamyl (linear) and isocinnamyl (branched) type substrates (4 and 5 -> 6), led to excellent regio- and enantioselectivities (> 30:1,

Original language	English
Pages (from-to)	6910-6929
Number of pages	20
Journal	Chemistry - A European Journal
Volume	12
Issue number	26
DOIs	https://doi.org/10.1002/chem.200501574
Publication status	Published - 6 Sep 2006

Keywords

allylic
substitution
asymmetric catalysis
chiral ligands
deuterium labeling
memory effect
molybdenum
SYN-ANTI DICHOTOMY
(PI-ALLYL)PALLADIUM COMPLEXES
OXIDATIVE ADDITION
1,10-PHENANTHROLINE LIGANDS
ALKYLATION REACTION
NEIGHBORING GROUPS
METAL-COMPLEXES
1ST OBSERVATION
AMINO-ACIDS
PALLADIUM

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10.1002/chem.200501574

Cite this

Malkov, A. V., Gouriou, L., Lloyd-Jones, G. C., Stary, I., Langer, V., Spoor, P., Vinader, V., & Kocovsky, P. (2006). Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction. Chemistry - A European Journal, 12(26), 6910-6929. https://doi.org/10.1002/chem.200501574

Malkov, Andrei V. ; Gouriou, Lanre ; Lloyd-Jones, Guy C. ; Stary, Ivo ; Langer, Vratislav ; Spoor, Paul ; Vinader, Victoria ; Kocovsky, Pavel. / Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum : Structural requirements of the ligand and the stereochemical course of the reaction. In: Chemistry - A European Journal. 2006 ; Vol. 12, No. 26. pp. 6910-6929.

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abstract = "Application of new chiral ligands (R)-(-)-12a and (S)-(+)-12c (VALDY), derived from amino acids, to the title reaction, involving cinnamyl (linear) and isocinnamyl (branched) type substrates (4 and 5 -> 6), led to excellent regio- and enantioselectivities (> 30:1,",

keywords = "allylic, substitution, asymmetric catalysis, chiral ligands, deuterium labeling, memory effect, molybdenum, SYN-ANTI DICHOTOMY, (PI-ALLYL)PALLADIUM COMPLEXES, OXIDATIVE ADDITION, 1,10-PHENANTHROLINE LIGANDS, ALKYLATION REACTION, NEIGHBORING GROUPS, METAL-COMPLEXES, 1ST OBSERVATION, AMINO-ACIDS, PALLADIUM",

author = "Malkov, {Andrei V.} and Lanre Gouriou and Lloyd-Jones, {Guy C.} and Ivo Stary and Vratislav Langer and Paul Spoor and Victoria Vinader and Pavel Kocovsky",

year = "2006",

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day = "6",

doi = "10.1002/chem.200501574",

language = "English",

volume = "12",

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Malkov, AV, Gouriou, L, Lloyd-Jones, GC, Stary, I, Langer, V, Spoor, P, Vinader, V & Kocovsky, P 2006, 'Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum: Structural requirements of the ligand and the stereochemical course of the reaction', Chemistry - A European Journal, vol. 12, no. 26, pp. 6910-6929. https://doi.org/10.1002/chem.200501574

Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum : Structural requirements of the ligand and the stereochemical course of the reaction. / Malkov, Andrei V.; Gouriou, Lanre; Lloyd-Jones, Guy C.; Stary, Ivo; Langer, Vratislav; Spoor, Paul; Vinader, Victoria; Kocovsky, Pavel.

In: Chemistry - A European Journal, Vol. 12, No. 26, 06.09.2006, p. 6910-6929.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Asymmetric allylic substitution catalyzed by C-1-symmetrical complexes of molybdenum

T2 - Structural requirements of the ligand and the stereochemical course of the reaction

AU - Malkov, Andrei V.

AU - Gouriou, Lanre

AU - Lloyd-Jones, Guy C.

AU - Stary, Ivo

AU - Langer, Vratislav

AU - Spoor, Paul

AU - Vinader, Victoria

AU - Kocovsky, Pavel

PY - 2006/9/6

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N2 - Application of new chiral ligands (R)-(-)-12a and (S)-(+)-12c (VALDY), derived from amino acids, to the title reaction, involving cinnamyl (linear) and isocinnamyl (branched) type substrates (4 and 5 -> 6), led to excellent regio- and enantioselectivities (> 30:1,

AB - Application of new chiral ligands (R)-(-)-12a and (S)-(+)-12c (VALDY), derived from amino acids, to the title reaction, involving cinnamyl (linear) and isocinnamyl (branched) type substrates (4 and 5 -> 6), led to excellent regio- and enantioselectivities (> 30:1,

KW - allylic

KW - substitution

KW - asymmetric catalysis

KW - chiral ligands

KW - deuterium labeling

KW - memory effect

KW - molybdenum

KW - SYN-ANTI DICHOTOMY

KW - (PI-ALLYL)PALLADIUM COMPLEXES

KW - OXIDATIVE ADDITION

KW - 1,10-PHENANTHROLINE LIGANDS

KW - ALKYLATION REACTION

KW - NEIGHBORING GROUPS

KW - METAL-COMPLEXES

KW - 1ST OBSERVATION

KW - AMINO-ACIDS

KW - PALLADIUM

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JO - Chemistry - A European Journal

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