Sequential Organocatalytic Stetter and Michael-Aldol Condensation Reaction: Asymmetric Synthesis of Fully Substituted Cyclopentenes via a [1 + 2 + 2] Annulation Strategy

Hong, Bor‐Cherng; Dange, Nitin S.; Hsu, Che‐Sheng; Liao, Ju‐Hsiou

doi:10.1021/ol101969t

Cited by 68 publications

(17 citation statements)

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“…[52] As shown in Scheme 17, these fully substituted cyclopentene derivatives were obtained in moderate to good yields albeit as single diastereomers and with excellent enantioselectivities of up to 99% ee.…”

Section: Domino Michael-aldol Reactionsmentioning

confidence: 96%

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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Section: Domino Michael-aldol Reactionsmentioning

confidence: 96%

Recent Developments in Asymmetric Organocatalytic Domino Reactions

2012

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“…In the field of cyclopentane synthesis, Hong and coworkers developed an organocatalytic Stetter and Michael/ aldol reaction sequence. 20 Starting from heteroaromaticsubstituted β-nitro ketones 30 and α,β-unsaturated aldehydes, a [1+2+2] annulation strategy, previously used by the same research group to synthesize cyclopentenes, 21 was used to afford fully substituted cyclopentanols 31 bearing a quaternary stereocenter (Scheme 8). In this case, it was crucial to have heteroaromatic aldehydes 28 as substrates to undergo the intermolecular Stetter reaction with nitroalkenes 29 in order to prepare the nitro ketone substrates 30.…”

Section: Syn Thesismentioning

confidence: 99%

Recent Advances in Organocatalytic Cascade Reactions toward the Formation of Quaternary Stereocenters

et al. 2015

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“…The carbene generated from the thiazolium salt 1a catalyzed the Stetter reaction, and the chiral proline derivative 46 catalyzed the Michael-aldol condensation sequence (Scheme 32). 60 Overall, the protocol represents an organocatalytic formal [1+2+2] annulation reaction for the simple and direct stereoselective construction of fully functionalized cyclopentenes. Interestingly, when the reaction was carried out using heteroaromatic aldehydes such as picolinaldehyde, the reaction followed a sequential Stetter and Michael-aldol reaction leading to the synthesis of fully substituted cyclopentanols.…”

Section: Scheme 29 Enzymatic Intermolecular Stetter Reactionmentioning

confidence: 99%