Organocatalytic asymmetric synthesis of polyfunctionalized 3-(cyclohexenylmethyl)-indoles via a quadruple domino Friedel–Crafts-type/Michael/Michael/aldol condensation reaction

Enders, Dieter; Wang, Chuan; Mukanova, M. S.; Greb, Andreas

doi:10.1039/c002839h

Cited by 100 publications

(22 citation statements)

References 61 publications

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“…A four‐component sequential Friedel–Crafts/Michael/Michael/aldol condensation process was reported by Enders and co‐workers 225. Highly substituted cyclohexene‐carboxaldehydes were obtained with high degrees of enantioselectivity.…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 94%

“…A four-component sequential Friedel-Crafts/Michael/Michael/aldol condensation process was reported by Enders www.chemeurj.org and co-workers. [225] Highly substituted cyclohexene-carboxaldehydes were obtained with high degrees of enantioselectivity. The successful execution of this transformation depends on slow addition of acrolein 113.…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 99%

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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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Section: Multicomponent and Cascade Reactionsmentioning

confidence: 94%

Section: Multicomponent and Cascade Reactionsmentioning

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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“…[182] This novel process was based on a quadruple domino Friedel-Crafts-Michael-Michael-aldol condensation reaction catalyzed by chiral amine (S)-3. As shown in Scheme 105, the products 401a-i were produced in moderate to excellent yields (23-82%) and excellent diastereo-and enantioselectivities of up to > 90% de, and > 99% ee, respectively.…”

Section: Miscellaneous Multicomponent 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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“…Therefore, in the last few years, MCRs were developed as a fast and convenient way for efficient synthesis of organic compounds [10][11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%