Enantioselective Construction of Pyrimidine‐Fused Diazepinone Derivatives Bearing a Tertiary Stereogenic Center Enabled by Iridium‐Catalysed Intramolecular Allylic Substitution

Construction of a quaternary stereogenic center was accomplished through the enantioselective intramolecular allylic substitution reaction of bis-trichloroacetimidate catalyzed by a chiral phosphoramide derivative.

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Exploration of Aryllithium-Derived Copper Reagents for Quaternary-Stereogenic-Center-Forming Allylic Substitution of γ,γ-Disubstituted Secondary Allylic Picolinates

Synlett ◽

10.1055/s-0035-1560907 ◽

2015 ◽

Vol 27 (04) ◽

pp. 611-615 ◽

Cited By ~ 2

Author(s):

Yuichi Kobayashi ◽

Takuri Ozaki

Keyword(s):

Allylic Substitution ◽

Stereogenic Center

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ChemInform Abstract: Exploration of Aryllithium-Derived Copper Reagents for Quaternary-Stereogenic-Center-Forming Allylic Substitution of γ,γ-Disubstituted Secondary Allylic Picolinates.

ChemInform ◽

10.1002/chin.201628058 ◽

2016 ◽

Vol 47 (28) ◽

Author(s):

Takuri Ozaki ◽

Yuichi Kobayashi

Keyword(s):

Allylic Substitution ◽

Stereogenic Center

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Construction of P-Stereogenic Center by Selective Ligation of N—P—N Type Ligands and Application to Asymmetric Allylic Substitution Reactions.

ChemInform ◽

10.1002/chin.200410025 ◽

2004 ◽

Vol 35 (10) ◽

Author(s):

Takamichi Yamagishi ◽

Masatoshi Ohnuki ◽

Takahiro Kiyooka ◽

Dai Masui ◽

Kiyoshi Sato ◽

...

Keyword(s):

Allylic Substitution ◽

Substitution Reactions ◽

Stereogenic Center

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NeoPHOX – a structurally tunable ligand system for asymmetric catalysis

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.12.114 ◽

2016 ◽

Vol 12 ◽

pp. 1185-1195 ◽

Cited By ~ 8

Author(s):

Jaroslav Padevět ◽

Marcus G Schrems ◽

Robin Scheil ◽

Andreas Pfaltz

Keyword(s):

Asymmetric Catalysis ◽

Asymmetric Hydrogenation ◽

Tertiary Alcohol ◽

Allylic Substitution ◽

Ligand System ◽

Methoxycarbonyl Group ◽

Palladium Catalyzed ◽

Stereogenic Center

A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesium chloride leads to a tertiary alcohol, which can be acylated or silylated to produce NeoPHOX ligands with different sterical demand. The new NeoPHOX ligands were tested in the iridium-catalyzed asymmetric hydrogenation and palladium-catalyzed allylic substitution. In both reactions high enantioselectivities were achieved, that were comparable to the enantioselectivities obtained with the up to now best NeoPHOX ligand derived from expensive tert-leucine.

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