Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones

Hong, Bor‐Cherng; Kotame, Prakash; Liao, Ju‐Hsiou

doi:10.1039/c0ob00834f

Cited by 72 publications

(26 citation statements)

References 88 publications

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“…8, 152.2, 134.4, 132.2, 129.9, 129.1, 128.4, 123.0, 122.6, 120.2, 117.5, 87.2, 65.2, 43.4, 42.8, 41.4, 39 2, 134.8, 133.9, 129.5, 129.3, 129.0, 128.4, 122.5, 120.2, 117.5, 87.3, 65.2, 43.4, 15 42.7, 41.5, 39.0 ppm; IR (KBr): v % 1724, 1689,1546,1489,1456,1280,1249,1229,1125,1093,1068,1014,839,811,7753,707,666,541,514 4, 138.7, 132.4, 35 129. 2, 131.2, 131.0, 130.3, 123.6, 123.5, 122.4, 118.7, 114.0, 113.6, 91.9, 66.9, 57.1, 57.0, 47.0, 45.7, 43.6, 37.9 ppm;IR (KBr): v % 1720, 1587, 1544, 1518, 1491, 1460, 1347, 1246, 1147, 1072, 1023 8,154.4,152.4,131.2,130.7,130.2,125.7,123.8,123.5,118.7,114.1,91.9,67.1,47.1,45.6,43.8,41.3,37.9 ppm;IR (KBr): v % 85 1709,1611,…”

Section: Methodsmentioning

confidence: 99%

Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives

2015

Org. Biomol. Chem.

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An efficient protocol for the asymmetric construction of enantiomerically enriched tetrahydro-6H-benzo[c]chromenes and their derivatives has been developed. The corresponding products were obtained by the cascade double Michael addition of 3-nitro-2H-chromenes and their derivatives with α,β-unsaturated ketones catalyzed by a combination of a quinine-derived primary amine and benzoic acid. Through this methodology, the desired products could be obtained in moderate to good yields (up to 90%), with excellent diastereoselectivities (up to >25 : 1 dr) and moderate to excellent enantioselectivities (up to 95% ee).

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Section: Methodsmentioning

confidence: 99%

Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives

2015

Org. Biomol. Chem.

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“…[80] have independently reported asymmetric domino Michael-hemiacetalization reactions of 2-hydroxynitrostyrenes 161a and 161b with aliphatic aldehydes catalyzed by simple chiral catalyst (S)-3 combined with benzoic acid in 95% EtOH or water only as solvent. These reactions afforded, after a subsequent oxidation with PCC, the corresponding 3,4-disubstituted dihydrocoumarins 162a-d as a mixture of cis and trans diastereomers.…”

Section: Domino Michael-intramolecular Heterocyclization Reactionsmentioning

confidence: 99%

Recent Developments in Asymmetric Organocatalytic Domino Reactions

2012

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Since about the year 2000, the research area of asymmetric organocatalysis has grown rapidly to become one of the most fascinating and current fields in organic chemistry. In the last years, asymmetric domino reactions have widely benefited from this fast-growing field, as exemplified by the development of an explosive number of novel and powerful asymmetric organocatalytic domino processes, which allowed the easy construction of complex chiral molecular architectures from simple materials with high yields and very often remarkable enantioselectivities in a metal-free environment. Indeed, the possibility to join two or more organocatalytic reactions in one asymmetric domino process has become a challenging goal for chemists, due to several advantages from economical and environmental points of view, avoiding costly protecting groups and time-consuming purification procedures after each step, for example. This review aims to update the latest developments of this hot and fascinating field, covering the literature since the beginning of 2009.

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“…A Michael/Henry sequence with terminal acetalisation yields enantiopure tetrahydro‐benzochromen‐6‐ones. Diphenylprolinolsilyl ether 87 catalyzes this cascade of glutaraldehyde 240 and nitroolefins (Scheme ) 274…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 99%

“…Diphenylprolinolsilyl ether 87 catalyzes this cascade of glutaraldehyde 240 and nitroolefins (Scheme 141). [274] For a successful execution of a Michael/intramolecular benzoin cascade a sequential deployment of two different Scheme catalysts is necessary. The first step, the Michael addition, is catalyzed by diphenylprolinolsilyl ether 87.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

200

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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Enantioselective organocatalytic domino Michael–acetalization–Henry reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of tetrahydro-6H-benzo[c]chromenones

Cited by 72 publications

References 88 publications

Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives

Enantioselective cascade double Michael addition of 3-nitro-2H-chromenes and acyclic enones: efficient synthesis of functionalized tricyclic chroman derivatives

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

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