The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis

Dijk, Ewold W.; Panella, Lavinia; Pinho, Pedro; Naasz, Robert; Meetsma, Auke; Minnaard, Adriaan J.; Feringa, Ben L.

doi:10.1016/j.tet.2004.06.148

Cited by 78 publications

(33 citation statements)

References 57 publications

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“…Tremendous chiral metal complexes have been synthesized and applied to many types of catalytic asymmetric reactions. However, the combination of different metal catalysts for catalytic asymmetric reactions is rather limited, probably owing to the fact that the presence of multiple metal catalysts will lead to the competitive coordination of metals to the chiral ligand used, which makes the chiral environmental unpredictable and un- [4] the key step of which is a Cu/Pd catalyzed tandem asymmetric conjugate addition-allylic substitution reaction (Scheme 1). To prevent the possible catalyst interference, the palladium catalyst was added after the completion of the catalytic asymmetric Michael addition of Me 2 Zn to cyclohexenone 1.…”

Section: By Multiple Metal Catalystsmentioning

confidence: 99%

Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions

Zhou

2010

Chemistry An Asian Journal

443

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Dedicated to the 150th anniversary of Japan-UK diplomatic relations FOCUS REVIEWSAbstract: Multicatalyst promoted asymmetric tandem reactions have emerged as a powerful strategy to improve the synthetic efficiency. It enables the synthesis of complex molecules with high selectivity from simple starting materials in an almost biomimetic-like way. The use of multiple catalyst systems can enlarge the substrate and reaction scope for the reaction design, improve the reactivity, and benefit the control of selectivity. In this FocusReview, the current achievement of this promising field is discussed, including the advantages and difficulties of this research, and the strategies applied to address these problems.

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Section: By Multiple Metal Catalystsmentioning

confidence: 99%

Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions

Zhou

2010

Chemistry An Asian Journal

443

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“…The usefulness of this idea has been demonstrated by the trapping of enolates with aldehydes, [12] allylic cations, [13] nitroso compounds, [14] bromine, [15] or acid anhydrides. [16] Metal enolates were also enantioselectively protonated.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective One‐Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

2010

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Asymmetric addition of Grignard reagents to cyclohexenone, catalyzed by ferrocene diphosphanes, afforded chiral magnesium enolates. These enolates reacted in a one‐pot arrangement with N‐benzylidenetoluenesulfonamide to give β‐amino carbonyl compounds with three contiguous stereocenters. Two major diastereoisomers (dr = 60:40) of product with enantioselectivities up to 95 % ee were separated by flash chromatography.

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“…Inherent in any multiple catalyst system is the challenge of compatibility. Avoidance of mutual interference often obliges stepwise addition of catalysts or reagents and variation of reaction conditions over time (21)(22)(23)(24)(25)(26). Nevertheless, cascades triggered by a single operation have been accomplished (20,27,28).…”

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confidence: 99%

Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes

Filloux

Lathrop²,

Rovis³

2010

Proc. Natl. Acad. Sci. U.S.A.

128

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We report the development of a multicatalytic, one-pot, asymmetric Michael/Stetter reaction between salicylaldehydes and electrondeficient alkynes. The cascade proceeds via amine-mediated Michael addition followed by an N-heterocyclic carbene-promoted intramolecular Stetter reaction. A variety of salicylaldehydes, doubly activated alkynes, and terminal, electrophilic allenes participate in a one-step or two-step protocol to give a variety of benzofuranone products in moderate to good yields and good to excellent enantioselectivities. The origin of enantioselectivity in the reaction is also explored; E∕Z geometry of the reaction intermediate as well as the presence of catalytic amounts of catechol additive are found to influence reaction enantioselectivity.catalysis | organic synthesis | tandem catalysis

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The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis

Abstract: The potent neurotoxin (K)-pumiliotoxin C has been prepared in 8 steps starting from 2-cyclohexenone. Key steps are a tandem asymmetric conjugate addition-allylic substitution reaction and a tandem Heck-allylic substitution reaction. q

Cited by 78 publications

References 57 publications

Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions

Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions

Enantioselective One‐Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes

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