Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an Aluminum complex of a newly prepared chiral menthol derivative

Naraku, G.; Hori, Kiyoto; Ito, Yoshio; Katsuki, Tsutomu

doi:10.1016/s0040-4039(97)10202-7

Cited by 27 publications

(6 citation statements)

References 8 publications

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“…This review aims to compile the work based on selectivity in cycloaddition protocols to generate a systematic, synthetically valuable composition in organic synthesis, inspired by the distinct results accumulated by the DA reaction. Furthermore, the review explains how to access a wide range of compounds by comprehending the stereocontrol aid supplied by intrinsic and extrinsic characteristics [46,47] . The review focuses on the most significant discoveries in this area from 2000 to the present, and it summarizes the aid provided to manage site selectivity in DA pursuits.…”

Section: Selectivity In Diels‐alder Cycloaddition Pathwaymentioning

confidence: 99%

“…Furthermore, the review explains how to access a wide range of compounds by comprehending the stereocontrol aid supplied by intrinsic and extrinsic characteristics. [46,47] The review focuses on the most significant discoveries in this area from 2000 to the present, and it summarizes the aid provided to manage site selectivity in DA pursuits. As aforementioned, the review is further classified into the following categories based on the impact of controlling the selectivity used in the DA cycloaddition route: I Selectivity influence by dienophile molecular arrangement, II Selectivity influence by diene molecular arrangement, III Selectivity influence by diene and dienophile molecular arrangement, IV Selectivity influence by intrinsic parameters pertaining diene and dienophile both, V Selectivity influence by extrinsic parameters pertaining diene and dienophile.…”

Section: Selectivity In Diels-alder Cycloaddition Pathwaymentioning

confidence: 99%

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Regioselectivity Switch Towards the Development of Innovative Diels‐Alder Cycloaddition and Productive Applications in Organic Synthesis

2022

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The Diels‐Alder (DA) reaction is one of the fascinating synthetic strategies known for its pericyclic action and concerted mechanism that leads to various targets. Numerous synthetic pursuits have been rewarded with conceptually distinct and efficient ways. To date, extensive and spectacular accomplishments have been made in the field of Diels‐Alder chemistry to overcome the complexities of organic synthesis that inspired organic chemists to focus on expanding and establishing the postulates. In principle, DA reactions are governed by their straightforward reactivity pattern with a high degree of certainty, primarily attributed to the HOMO‐LUMO separation of reacting partners. Furthermore, general forecasts rely on account of background studies, conveniently hypothesizing the stereochemical outcomes and reaction dynamic pathways. DA has recently emerged as a technique for establishing a variety of products from the same reacting species under varying reaction conditions rather than a general reactivity profile. Such exceptional results are of significant interest in organic synthesis to pursue the challenges of unanticipated product establishment. Herein, we summarize the impressive finding of the remarkable switch in the regioselectivity and diastereoselectivity of DA reactions under a diverse set of reaction protocols in light of Diels‐Alder's unending importance in chemical science. This review aims to establish a beneficial account of Diels‐Alder towards the astonishing switches extended to study varying synthetic versions in organic synthesis protocols attributed to natural and biologically active scaffolds. This review also provides insight into distinct reaction dynamics in DA reactions that are subjected to access molecular frameworks ranging from simple to complicated ones to foster high levels of innovation in chemical sciences.

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Section: Selectivity In Diels‐alder Cycloaddition Pathwaymentioning

confidence: 99%

Section: Selectivity In Diels-alder Cycloaddition Pathwaymentioning

confidence: 99%

Regioselectivity Switch Towards the Development of Innovative Diels‐Alder Cycloaddition and Productive Applications in Organic Synthesis

2022

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“…trunsPiperylene and 1-methoxybutadiene were reacted with n-butyl glyoxalate and diethyl mesoxalate; the results are summarized in Sch. 46. The asymmetric induction and chemical yield in these reactions are quite poor but the authors did find that moderate asymmetric induction could be obtained from reactions catalyzed by Eu(hfc)3.…”

Section: Heteroatom Diels-alder Reactionsmentioning

confidence: 99%

“…A very interesting recent report describes the effect of a catalyst prepared from ethylaluminum dichloride and the diol 199 on the reaction of dienophile 197 with cyclopentadiene [46]. A single catalyst was found to give high asymmetric induction for either enantiomer of the endo adduct 198.…”

Section: Scheme 20mentioning

confidence: 99%

Chiral Aluminum Lewis Acids in Organic Synthesis

Wulff

2000

Lewis Acids in Organic Synthesis

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The earliest report of a reaction mediated by a chiral three coordinate aluminum species describes an asymmetric Meerwein-Ponndorf-Verley reduction of ketones with chiral aluminum alkoxides which resulted in low induction in the alcohol products [1]. Subsequent developments in the area were sparse until over a decade later when chiral aluminum Lewis acids began to be explored in polymerization reactions, with the first report describing the polymerization of benzofuran with catalysts prepared from and ethylaluminum dichloride and a variety of chiral compounds including /3-phenylalanine [2]. Curiously, these reports did not precipitate further studies at the time because the next development in the field did not occur until nearly two decades later when Hashimoto, Komeshima and Koga reported that a catalyst derived from ethylaluminum dichloride and menthol catalyzed the asymmetric Diels-Alder reaction shown in Sch. 1 [3,4]. This is especially curious because the discovery that a Diels-Alder reaction could be accelerated by aluminum chloride was known at the time the polymerization work appeared [5]. Perhaps it was because of this long delay, that the report of this asymmetric catalytic Diels-Alder reaction was to become the inspiration for the dramatic increase in activity in this field that we have witnessed in the twenty years since its appearance. It is the intent of this review to present the development of the field of asymmetric catalytic synthesis with chiral aluminum Lewis acids that includes those reports that have appeared in the literature up to the end of 1998. This review will not cover polymerization reactions or supported reactions. The latter will appear in a separate chapter in this handbook. 15 rnol % catalyst 4 toluene, -78 OC, 3 h 0 2 1.1 equiv 3 69 % yield exo : endo = 98 : 2 72 % ee 1 EtAlC12 . OAIC12 A A 5 4 Scheme 1

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“…Not many 1,3-diols have been demonstrated to function as efficient ligands in metal-induced asymmetric catalysis. Amongst those reported are the aluminium complexes of the menthone and isomenthone-derived 1,3-diols, which were successfully applied to the asymmetric Diels-Alder reaction of 3-crotonoyl-2-oxazolidinone and cyclopentadiene 19 and to the Mukaiyama aldol reaction of the TMS enol ether of methyl isobutyrate and isobutyraldehyde, 20 respectively. Several bicyclo [2.2.2]octane-diol (BODOL) ligands have been reported to work as efficient asymmetric catalysts in the titanium catalyzed catecholborane (CBH) reduction of ketones [21][22][23] and in the diethylzinc addition to aromatic aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Bicyclo[2.2.2]octane-derived chiral ligands—synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane

Friberg

Sarvary

Wendt

et al. 2008

Tetrahedron: Asymmetry

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Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an Aluminum complex of a newly prepared chiral menthol derivative

Cited by 27 publications

References 8 publications

Regioselectivity Switch Towards the Development of Innovative Diels‐Alder Cycloaddition and Productive Applications in Organic Synthesis

Regioselectivity Switch Towards the Development of Innovative Diels‐Alder Cycloaddition and Productive Applications in Organic Synthesis

Chiral Aluminum Lewis Acids in Organic Synthesis

Bicyclo[2.2.2]octane-derived chiral ligands—synthesis and application of BODOLs in the asymmetric reduction of acetophenone with catecholborane

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