Efficient catalytic asymmetric alkylations. 3. A kinetic and mechanistic study of the enantioselective phase-transfer methylation of 6,7-dichloro-5-methoxy-2-phenyl-1-indanone

1987 ◽  
Vol 52 (21) ◽  
pp. 4745-4752 ◽  
Author(s):  
D. L. Hughes ◽  
U. H. Dolling ◽  
K. M. Ryan ◽  
E. F. Schoenewaldt ◽  
E. J. J. Grabowski
Keyword(s):  
Phase Transfer ◽  
Mechanistic Study ◽  
Catalytic Asymmetric ◽  
Asymmetric Alkylations

scholarly journals Catalytic Asymmetric Intramolecular Darzens Reaction of 2-Halomalonate Derivatives

2019 ◽  
Vol 14 (10) ◽  
pp. 1934578X1988440
Author(s):  
Kenichi Kobayashi ◽  
Kosaku Tanaka ◽  
Momoko Suzuki ◽  
Hiroshi Kogen
Keyword(s):  
Natural Products ◽  
Natural Product ◽  
Phase Transfer ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Darzens Reaction ◽  
Phase Transfer Catalysts ◽  
Catalytic Asymmetric

A catalytic asymmetric intramolecular Darzens reaction of 2-halomalonate derivatives was developed for the enantioselective preparation of chiral building blocks for epoxide-containing natural products. Among the screened catalysts, some phase-transfer catalysts gave the desired epoxide in moderate enantioselectivity, albeit in low yield. The epoxide product would be useful as versatile chiral building blocks for natural product synthesis.

Catalytic asymmetric total synthesis of (+)-artalbic acid

2016 ◽  
Vol 52 (60) ◽  
pp. 9391-9393 ◽  
Author(s):  
Toyoharu Kobayashi ◽  
Ryuta Shioi ◽  
Ai Ushie ◽  
Hideki Abe ◽  
Hisanaka Ito
Keyword(s):  
Total Synthesis ◽  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Asymmetric Allylation ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric

The first total synthesis of (+)-artalbic acid has been accomplished using asymmetric allylation of an acetoacetate derivative with a phase-transfer catalyst.

scholarly journals Epoxide Syntheses and Ring-Opening Reactions in Drug Development

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1117
Author(s):  
Fotini Moschona ◽  
Ioanna Savvopoulou ◽  
Maria Tsitopoulou ◽  
Despoina Tataraki ◽  
Gerasimos Rassias
Keyword(s):  
Ring Opening ◽  
Large Scale ◽  
Phase Transfer ◽  
Hiv Protease ◽  
Main Stream ◽  
Hiv Protease Inhibitors ◽  
Chiral Phase ◽  
Diverse Range ◽  
Ring Opening Reactions ◽  
Catalytic Asymmetric

This review concentrates on success stories from the synthesis of approved medicines and drug candidates using epoxide chemistry in the development of robust and efficient syntheses at large scale. The focus is on those parts of each synthesis related to the substrate-controlled/diastereoselective and catalytic asymmetric synthesis of epoxide intermediates and their subsequent ring-opening reactions with various nucleophiles. These are described in the form of case studies of high profile pharmaceuticals spanning a diverse range of indications and molecular scaffolds such as heterocycles, terpenes, steroids, peptidomimetics, alkaloids and main stream small molecules. Representative examples include, but are not limited to the antihypertensive diltiazem, the antidepressant reboxetine, the HIV protease inhibitors atazanavir and indinavir, efinaconazole and related triazole antifungals, tasimelteon for sleep disorders, the anticancer agent carfilzomib, the anticoagulant rivaroxaban the antibiotic linezolid and the antiviral oseltamivir. Emphasis is given on aspects of catalytic asymmetric epoxidation employing metals with chiral ligands particularly with the Sharpless and Jacobsen–Katsuki methods as well as organocatalysts such as the chiral ketones of Shi and Yang, Pages’s chiral iminium salts and typical chiral phase transfer agents.

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