Chiral Amino Alcohol Derived Bis-phosphoramidite Pincer Palladium Complexes and Their Applications in Asymmetric Allylation of Aldimines

2010 ◽  
Vol 29 (6) ◽  
pp. 1379-1387 ◽  
Author(s):  
Jie Li ◽  
Martin Lutz ◽  
Anthony L. Spek ◽  
Gerard P. M. van Klink ◽  
Gerard van Koten ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Palladium Complexes ◽  
Asymmetric Allylation

ChemInform Abstract: Asymmetric Allylation of Sulfonyl Imines Catalyzed by in situ Generated Cu(II) Complexes of Chiral Amino Alcohol Based Schiff Bases.

ChemInform ◽  
2015 ◽  
Vol 46 (16) ◽  
pp. no-no
Author(s):  
Debashis Ghosh ◽  
Prasanta Kumar Bera ◽  
Manish Kumar ◽  
Sayed H. R. Abdi ◽  
Noor-ul H. Khan ◽  
...  
Keyword(s):  
Schiff Bases ◽  
Amino Alcohol ◽  
Asymmetric Allylation

Asymmetric allylation of sulfonyl imines catalyzed by in situ generated Cu(ii) complexes of chiral amino alcohol based Schiff bases

RSC Advances ◽  
2014 ◽  
Vol 4 (99) ◽  
pp. 56424-56433 ◽  
Author(s):  
Debashis Ghosh ◽  
Prasanta Kumar Bera ◽  
Manish Kumar ◽  
Sayed H. R. Abdi ◽  
Noor-ul H. Khan ◽  
...  
Keyword(s):  
Schiff Base ◽  
Schiff Bases ◽  
Amino Alcohol ◽  
Enantioselective Synthesis ◽  
Asymmetric Allylation

We have developed a catalytic route for enantioselective synthesis of homoallyl amines through Cu(ii)-Schiff base catalyzed allylation of aryl N-sulfonylimines.

Synthesis and Reactivity of Precolibactin 886

2019 ◽  
Author(s):  
Seth Herzon ◽  
Alan R. Healy ◽  
kevin wernke ◽  
Chung Sub Kim ◽  
Nicholas Lees ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Gene Cluster ◽  
Amino Alcohol ◽  
Biomimetic Synthesis ◽  
Cross Linking ◽  
E Coli ◽  
Hplc Purification ◽  
Structural Assignment ◽  
Biosynthetic Precursor ◽  
Double Oxidation

<div>The clb gene cluster encodes the biosynthesis of metabolites known as precolibactins and colibactins. The clb pathway is found in gut commensal E. coli, and clb metabolites are thought to initiate colorectal cancer via DNA cross-linking. Precolibactin 886 (1) is one of the most complex isolated clb metabolites; it contains a 15-atom macrocycle and an unusual 5-hydroxy-3-oxazoline ring. Here we report confirmation of the structural assignment via a biomimetic synthesis of precolibactin 886 (1) proceeding through the amino alcohol 9. Double oxidation of 9 afforded the unstable α-ketoimine 2 which underwent macrocyclization to precolibactin 886 (1) upon HPLC purification (3% from 9). Studies of the putative precolibactin 886 (1) biosynthetic precursor 2, the model α-ketoimine 25, and the α-dicarbonyl 26 revealed that these compounds are susceptible to nucleophilic rupture of the C36–C37 bond. Moreover, cleavage of 2 produces other known clb metabolites or biosynthetic intermediates. This unexpected reactivity explains the difficulties in isolating full clb metabolites and accounts for the structure of a recently identified colibactin–adenine adduct. The colibactin peptidase ClbP deacylates synthetic precolibactin 886 (1) to form a non-genotoxic pyridone, suggesting precolibactin 886 (1) lies off-path of the major biosynthetic route.</div>

A Short, Affordable, One-Pot Synthesis of a Camphor-Derived Amino Alcohol

1995 ◽  
Vol 25 (19) ◽  
pp. 2975-2980 ◽  
Author(s):  
Robert M. Przeslawski ◽  
Suzanne Newman ◽  
Edward R. Thornton ◽  
Madeleine M. Joullié
Keyword(s):  
Amino Alcohol ◽  
One Pot ◽  
One Pot Synthesis

Synergistic Cu/Pd-Catalyzed Asymmetric Allylation: A Facile Access to α-Quaternary Cysteine Derivatives

2021 ◽  
Author(s):  
Hui-Min Wu ◽  
Zongpeng Zhang ◽  
Liang Wei ◽  
Xiu-Qin Dong ◽  
Chun-Jiang Wang
Keyword(s):  
Asymmetric Allylation ◽  
Synthetic Methodology ◽  
Asymmetric Catalytic

An efficient synthetic methodology to access biologically important and synthetically useful α-quaternary cysteine derivatives via asymmetric catalytic α-allylation of readily available 2-thiazoline-4-carboxylates was successfully developed through the synergistic Cu/Pd catalytic...

Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2013-2017
Author(s):  
Akira Sakakura ◽  
Yudai Fujii ◽  
Ryota Nakao ◽  
Saki Sugihara ◽  
Keita Fujita ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Danishefsky's Diene

AbstractAn enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

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