Rhodium-Catalyzed Asymmetric [4 + 1] Cycloaddition

Murakami, Masahiro; Itami, and Kenichiro; Ito, Yoshihiko

doi:10.1021/ja964259m

Cited by 67 publications

(22 citation statements)

References 13 publications

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“…In the addition of Et 2 Zn to N-diphenylphosphinoylimines good enantioselectivities (85-96 %ee) have been obtained with a Cu(II)-catalyst based on Me-DuPHOS [106]. This ligand showed also reasonable stereodiscriminating ability in the Ptmediated [4+1] cycloaddition of vinylallenes with CO (64-79 %ee) [107]. A recent application of DuPHOS was concerned to the Pt-catalyzed Bayer-Villiger oxidation of a substituted meso cyclohexanone with aqueous H 2 O 2 as oxidant (73 %ee) [108].…”

Section: Bis(phospholanes)mentioning

confidence: 96%

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Holz¹,

Gensow²,

Zayas

et al. 2007

COC

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Section: Bis(phospholanes)mentioning

confidence: 96%

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Holz¹,

Gensow²,

Zayas

et al. 2007

COC

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“…266 Finally an unusual [4ϩ1] cycloaddition reaction was reported by Ito and coworkers. 267 The Rh-DUPHOS catalysed reaction between CO and a vinyl allene proceeded with up to 92% ee (Scheme 51), although poorer selectivity was observed for allene substrates which did not contain an ester group.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

Asymmetric catalysts

Wills¹,

Tye²

1999

J. Chem. Soc., Perkin Trans. 1

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“…On the basis of previous reports and this work, we have proposed a reaction mechanism for the Rh I ‐catalyzed [4+1] cycloaddition of propargylic acetates (Scheme ). The coordination of the Rh I center to 7 followed by the metal‐promoted migration of the acetate group generates the allene intermediate 9 .…”

Section: Resultsmentioning

confidence: 97%

Diastereoselective [4+1] Cycloaddition of Alkenyl Propargylic Tertiary Acetates with CO Catalyzed by [RhCl(CO)₂]₂

Zhang

Zhao

2017

Eur J Org Chem

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Alkenyl propargylic tertiary acetates were prepared by deprotonation of the corresponding enyne followed by nucleophilic addition to ketones and then treatment with acetic anhydride. The resulting acetates were then employed in diastereoselective [4+1] cycloadditions with CO catalyzed by [RhCl(CO)2]2 to form α‐benzylidene cyclopentenone derivatives. We found the cycloadditions of the tertiary acetates to be more diastereoselective than those of the corresponding secondary acetates, as a result of increased substitution at the propargylic carbon. When an electron‐donating meta substituent, such as Me and MeO, is introduced to the aryl group at the propargylic carbon of the tertiary acetate, the diastereoselectivity improved to >8:1 (E/Z).

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Rhodium-Catalyzed Asymmetric [4 + 1] Cycloaddition

Cited by 67 publications

References 13 publications

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Asymmetric catalysts

Diastereoselective [4+1] Cycloaddition of Alkenyl Propargylic Tertiary Acetates with CO Catalyzed by [RhCl(CO)₂]₂

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Rhodium-Catalyzed Asymmetric [4 + 1] Cycloaddition

Cited by 67 publications

References 13 publications

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Asymmetric catalysts

Diastereoselective [4+1] Cycloaddition of Alkenyl Propargylic Tertiary Acetates with CO Catalyzed by [RhCl(CO)2]2

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Diastereoselective [4+1] Cycloaddition of Alkenyl Propargylic Tertiary Acetates with CO Catalyzed by [RhCl(CO)₂]₂