ChemInform Abstract: Preparation of Ester Group Substituted Allylic Zinc by Palladium-Catalyzed Umpolung of γ-Acyloxy-α,β-unsaturated Ester by Bis(iodozincio)methane.

ChemInform ◽  
2010 ◽  
Vol 41 (28) ◽  
pp. no-no
Author(s):  
Shizue Ueno ◽  
Mutsumi Sada ◽  
Seijiro Matsubara
Keyword(s):  
Ester Group ◽  
Unsaturated Ester ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Reductive Ring Opening with Formic Acid of Aziridines Bearing an α,β-Unsaturated Ester Group.

ChemInform ◽  
2010 ◽  
Vol 29 (5) ◽  
pp. no-no
Author(s):  
H. OHNO ◽  
N. MIMURA ◽  
A. OTAKA ◽  
H. TAMAMURA ◽  
N. FUJII ◽  
...  
Keyword(s):  
Formic Acid ◽  
Ring Opening ◽  
Ester Group ◽  
Unsaturated Ester ◽  
Palladium Catalyzed

Palladium-catalyzed reductive ring opening with formic acid of aziridines bearing an α,β-unsaturated ester group

Tetrahedron ◽  
1997 ◽  
Vol 53 (38) ◽  
pp. 12933-12946 ◽  
Author(s):  
Hiroaki Ohno ◽  
Norio Mimura ◽  
Akira Otaka ◽  
Hirokazu Tamamura ◽  
Nobutaka Fujii ◽  
...  
Keyword(s):  
Formic Acid ◽  
Ring Opening ◽  
Ester Group ◽  
Unsaturated Ester ◽  
Palladium Catalyzed

scholarly journals THREE NEW DAPHNIPHYLLUM ALKALOIDS WITH AN αβ,γδ-UNSATURATED ESTER GROUP FROMDAPHNIPHYLLUM GRACILEGAGE

1980 ◽  
Vol 9 (4) ◽  
pp. 393-396 ◽  
Author(s):  
Shosuke Yamamura ◽  
J. A. Lamberton ◽  
Masatake Niwa ◽  
Keiko Endo ◽  
Yoshimasa Hirata
Keyword(s):  
Ester Group ◽  
Unsaturated Ester

Practical Early Development Synthesis of Nav1.7 Inhibitor GDC-0310

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3406-3414 ◽  
Author(s):  
Andreas Stumpf ◽  
Frédéric St-Jean ◽  
David Lao ◽  
Zhigang Ken Cheng ◽  
Remy Angelaud ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Early Development ◽  
Enantiomeric Excess ◽  
Coupling Reaction ◽  
Active Pharmaceutical Ingredient ◽  
Ester Group ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Aromatic Bromination ◽  
Displacement Approach

The concise early development route to the Nav1.7 inhibitor GDC-0310 is described. The active pharmaceutical ingredient (API) contains one stereocenter, which was obtained with high enantiomeric excess (>99:1) by using an SN2 displacement approach to connect two intermediates: a chiral benzyl alcohol and a piperidine. The synthesis of the piperidine building block proceeded via a regioselective SNAr reaction on 1-chloro-2,4-difluorobenzene by N-Boc-4-piperidinemethanol, followed by installation of the methyl ester group by electrophilic aromatic bromination and a palladium-catalyzed alkoxycarbonylation. A subsequent Suzuki–Miyaura cross-coupling reaction was then telescoped directly into cleavage of the Boc group to provide the advanced piperidine intermediate. The key feature of the synthesis is the highly selective SN2 displacement of the chiral mesylate of (R)-1-(3,5-dichlorophenyl)ethan-1-ol with the piperidine intermediate, followed by a chiral purity upgrade via the corresponding (1S)-(+)-camphorsulfonic acid salt. After standard hydrolysis of the methyl ester and CDI mediated amidation to couple the resulting acid with methanesulfonamide, enantiomerically pure GDC-0310 was obtained in high overall yield (37%) on a 6.5 kilogram scale.

scholarly journals A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds

2020 ◽  
Vol 11 (8) ◽  
pp. 2136-2140 ◽  
Author(s):  
Barry M. Trost ◽  
Zhijun Zuo ◽  
Johnathan E. Schultz ◽  
Nagaraju Anugula ◽  
Katherine A. Carr
Keyword(s):  
Carbonyl Compounds ◽  
Unsaturated Ester ◽  
Allylic Alkylation ◽  
Palladium Catalyzed

A palladium-catalyzed allylation of ester-derived boron enolates, which is prepared through 1,4-reduction of α,β-unsaturated ester analogues.

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