An Enantiomerically Pure Pyridine NC-Palladacycle Derived from [2.2]Paracyclophane

2014 ◽  
Vol 67 (3) ◽  
pp. 374 ◽  
Author(s):  
Jean E. Glover ◽  
Paul G. Plieger ◽  
Gareth J. Rowlands
Keyword(s):  
Suzuki Coupling ◽  
Aryl Chloride ◽  
Enantiomerically Pure

An enantiomerically pure planar chiral pyridine-based palladacycle was prepared from [2.2]paracyclophane in just four steps. The palladacycle shows potential in catalysis, mediating the Suzuki coupling of an aryl chloride. It also permits the ortho bromination of [2.2]paracyclophane, a reaction that can be hard to achieve selectively.

Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of Spongistatin 1 (Altohyrtin A)

2009 ◽  
Vol 74 (5) ◽  
pp. 651-769 ◽  
Author(s):  
Alain Braun ◽  
Il Hwan Cho ◽  
Stephane Ciblat ◽  
Dean Clyne ◽  
Pat Forgione ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Side Chain ◽  
Spongistatin 1 ◽  
Enantiomerically Pure ◽  
Altohyrtin A ◽  
Stereogenic Centers ◽  
Complex Building ◽  
Synthetic Effort

Enantioselective approaches to the construction of four complex building blocks of the structurally intricate marine macrolide known as spongistatin 1 are presented. The first phase of the synthetic effort relies on a practical approach to a desymmetrized, enantiomerically pure spiroketal ring system incorporating rings A and B. Concurrently, the C17–C28 subunit, which houses one-fifth of the stereogenic centers of the target in the form of rings C and D, was assembled via a composite of stereocontrolled aldol condensations. Once arrival at the entire C1–C28 sector had been realized, routes were devised to provide two additional highly functionalized sectors consisting of C29–C44 and C38–C51. A series of subsequent transformations including cyclization of the E ring and hydroboration to afford the B-alkyl intermediate for the key Suzuki coupling to append the side chain took advantage of efficient stereocontrol. Ultimately, complete assembly and functionalization of the western EF sector of spongistatin was thwarted by an inoperative Suzuki coupling step intended to join the side chain to the C29–C44 sector, and later because of complications due to protecting groups, which precluded the complete elaboration of the late stage C29–C51 intermediate.

scholarly journals High-Activity Catalysts for Suzuki Coupling and Amination Reactions with Deactivated Aryl Chloride Substrates:  Importance of the Palladium Source.

2003 ◽  
Vol 22 (13) ◽  
pp. 2810-2810 ◽  
Author(s):  
Robin B. Bedford ◽  
Catherine S. J. Cazin ◽  
Simon J. Coles ◽  
Thomas Gelbrich ◽  
Peter N. Horton ◽  
...  
Keyword(s):  
High Activity ◽  
Suzuki Coupling ◽  
Aryl Chloride

ChemInform Abstract: Tunable Palladium-FibreCats for Aryl Chloride Suzuki Coupling with Minimal Metal Leaching.

ChemInform ◽  
2009 ◽  
Vol 40 (11) ◽  
Author(s):  
Thomas J. Colacot ◽  
William A. Carole ◽  
Bruce A. Neide ◽  
Ajay Harad
Keyword(s):  
Suzuki Coupling ◽  
Metal Leaching ◽  
Aryl Chloride

Tunable Palladium-FibreCats for Aryl Chloride Suzuki Coupling with Minimal Metal Leaching

2008 ◽  
Vol 27 (21) ◽  
pp. 5605-5611 ◽  
Author(s):  
Thomas J. Colacot ◽  
William A. Carole ◽  
Bruce A. Neide ◽  
Ajay Harad
Keyword(s):  
Suzuki Coupling ◽  
Metal Leaching ◽  
Aryl Chloride

High-Activity Catalysts for Suzuki Coupling and Amination Reactions with Deactivated Aryl Chloride Substrates:  Importance of the Palladium Source

2003 ◽  
Vol 22 (5) ◽  
pp. 987-999 ◽  
Author(s):  
Robin B. Bedford ◽  
Catherine S. J. Cazin ◽  
Simon J. Coles ◽  
Thomas Gelbrich ◽  
Peter N. Horton ◽  
...  
Keyword(s):  
High Activity ◽  
Suzuki Coupling ◽  
Aryl Chloride

Enzymatic Synthesis of Enantiomerically Pure Chiral Synthons: Lipase-Catalyzed Resolution of (R/S, 4E)-2-Methyl-4-hexen-l-ol

Synlett ◽  
1991 ◽  
Vol 1991 (04) ◽  
pp. 310-312
Author(s):  
Patrizia Ferraboschi ◽  
Daria Brembilla ◽  
Paride Grisenti ◽  
Enzo Santaniello
Keyword(s):  
Enzymatic Synthesis ◽  
Enantiomerically Pure

Solid-phase Bromination and Suzuki Coupling of 2-Carboxyindoles

2001 ◽  
Vol 4 (6) ◽  
pp. 521-524 ◽  
Author(s):  
J. Tois ◽  
R. Franzen ◽  
O. Aitio ◽  
I. Laakso ◽  
J. Huuskonen ◽  
...  
Keyword(s):  
Solid Phase ◽  
Suzuki Coupling

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

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