A highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

Suttibut, Chonticha; Kohari, Yoshihito; Igarashi, Ko; Nakano, Hiroto; Hirama, Masafumi; Seki, Chigusa; Matsuyama, Haruo; Uwai, Koji; Takano, Nobuhiro; Okuyama, Yuko; Osone, Kenichi; Takeshita, Mitsuhiro; Kwon, Eunsang

doi:10.1016/j.tetlet.2011.06.109

Cited by 39 publications

(20 citation statements)

References 19 publications

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“…Enantioselective Diels–Alder reaction of 1,2‐dihydropyridine for Tamiflu intermediate : Chiral amino alcohol 308 catalysed Diels‐Alder reaction (Scheme ) of 1, 2‐dihydropyridines ( 306 ) with acrolein derivative 307 produced endo ‐DA adduct 309 as stated by Suttibut and coauthors. Use of Bn group for esterification enhanced the yield up to 83 % and 98 % ee in this DA reaction than phenyl group (68 %,>99 % ee ).…”

Section: Common Synthetic Approachesmentioning

confidence: 90%

Synthetic Advancement of Neuraminidase Inhibitor “Tamiflu”

2020

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Tamiflu (oseltamivir phosphate), clinically working antiviral chiral drug, is most effective against the infectious disease caused by both influenza A and B. It is also the last resort drug for the treatment of N1H1 virus infection at a high cost with minimal global availability. The current industrial method uses natural (‐)‐shikimic acid obtained from Chinese star anise and coffee beans, hence the limited natural resource and scarcity restricted the Tamiflu production. While most of the synthetic methods reported were composed of natural chiral pools and relatively low‐cost reagents, however, the industrial process is fundamentally limited to the use of hazardous azide or tedious purification methods. In case of an influenza outbreak, producing the Tamiflu according to its demand may be difficult. This document detailed the synthetic progress of chemistry over the last two decades emphasizing the starting materials, hazards of reagents, time needed, number of steps, and overall yields etc. for the interest in academia as well as industrial research.

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Section: Common Synthetic Approachesmentioning

confidence: 90%

Synthetic Advancement of Neuraminidase Inhibitor “Tamiflu”

2020

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“…Firstly, we examined the catalytic efficiency of TFA salts of β‐amino alcohols 5 in DA cycloaddition between 1,2‐dihydropyridines 6 and acroleins 7 . Interestingly, they showed dramatic reactivity, affording the DA adducts with excellent yields and enantioselectivities (up to 98 % yield, up to 98 % ee, Scheme ) . The same reactions in the presence of β‐amino alcohol 2 as catalyst and TFA as co‐catalyst did not afford any better results than the TFA salt catalyst 5 .…”

Section: Diels–alder Cycloadditionmentioning

confidence: 99%

Catalytic Efficiency of Primary β‐Amino Alcohols and Their Derivatives in Organocatalysis

et al. 2016

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Chiral primary β‐amino alcohols, constuting adjacently positioned Brønsted base and Brønsted acid sites, are emerging as very valuable bifunctional organocatalysts in a wide array of asymmetric organic transformations. Primary β‐amino alcohols represent inexpensive alternatives to other primary amino organocatalysts such as chiral diamines and cinchona‐alkaloid‐derived primary amines, being easy to synthesize and air‐stable and offering the potential for introduction of different functional groups and also for alteration of steric sites. Here we reveal the catalytic use of simple primary β‐amino alcohols and their derivatives as organocatalysts in Diels–Alder cycloaddition, aldol condensation, Michael addition, 1,3‐dipolar cycloaddition, the Morita–Baylis–Hillman reaction, cascade cyclization, allylation of isatins, Friedel–Crafts alkylation and epoxidation of olefins.

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“…47,48 Oxazoline derived from 1, linked at the terminal position of a substituted conjugated tetraene-1-carboxylic acid, acts as an effective chiral auxiliary in the 8π, 6π tandem electrocyclization affording bicyclo[6.2.0]octadiene products, dr 3:1. 49 Asymmetric Aldol and Henry Reactions.…”

Section: Rcho + Phmentioning

confidence: 99%