Studies of Palladium-Catalyzed Cross-Coupling Reactions for Preparation of Highly Hindered Biaryls Relevant to the Korupensamine/Michellamine Problem

Hoye, Thomas R.; Chen, Minzhang

doi:10.1021/jo960882d

Cited by 72 publications

(20 citation statements)

References 13 publications

(7 reference statements)

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“…The axially chiral biaryl structural motif is a prominent feature of a number of biologically active natural products such as vancomycin7–9 and korupensamine A10–12 (Figure 1). Biaryls that exhibit axial chirality appear in ligands such as BINOL13,14 and BINAP15,16 (Figure 1) have had a profound impact on asymmetric synthesis17,18 and in organocatalysis 19,20.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations

et al. 2010

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We report efficient syntheses of axially chiral biaryl amides in yields ranging from 80–92%, and with enantioselectivity in the range 88–94% ee employing an asymmetric Suzuki-Miyaura process with Pd(OAc)2 and KenPhos as ligand. These studies demonstrate that electron-rich and electron-deficient o-halobenzamides can be efficiently coupled with 2-methyl-1-naphthylboronic acid and 2-ethoxy-1-naphthylboronic acid. The yields and selectivities of the reactions are independent of the nature of halogen substituent on the benzamide coupling partner. Our investigations demonstrate that axially chiral heterocyclic and biphenyl compounds can also be synthesized with this methodology. We also report computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolyl boronic acid with naphthylphosphonate bromide that was reported in a previous publication (J. Am. Chem. Soc. 2000, 122, 12051–12052). These studies indicate that the stereoselectivity arises from a combination of weak -(C)H•••O interactions as well as steric interactions between the tolyl and naphthylphosphonate addends in the transition state for C-C coupling.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations

et al. 2010

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“…[11] However, it was essential in this case to use a boronate (12; Scheme 4), rather than the precursor boronic acid, which has good hydrolytic stability due to the presence of the OTIPS residue in this molecule. [11] However, it was essential in this case to use a boronate (12; Scheme 4), rather than the precursor boronic acid, which has good hydrolytic stability due to the presence of the OTIPS residue in this molecule.…”

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confidence: 99%

A Stereospecific, Intermolecular Biaryl-Coupling Approach to Korupensamine A En Route to the Michellamines

Lipshutz¹,

Keith²

1999

Angew. Chem. Int. Ed.

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“…The non-racemic tetrahydroisoquinoline (1R,3R)-3 or (1R,3R)-4 was prepared following the procedure described earlier by Hoye et al [18,19] and others [20,21]. Stannanes 1 and 2 were also prepared by us and separated by chromatography using neutral Alumina [22].…”

Section: Resultsmentioning

confidence: 99%

Synthetic analogs of dioncophylline and michellamines by stille coupling

Elgazwy

2006

Journal of Heterocyclic Chemistry

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Dioncophielline and Michellamine Analogs S-5, R-5, S-7, R-7, S,S-8, R,R-8 and R,S-8 were synthesized by using Stille coupling condition (Pd°-mediated cross coupling) proceeds in low yield when using stannanes 1 or 2 with tetrahydroisoquinolinyl bromide 3. The addition of tetrahydroisoquinolinyl iodide 4 instead of 3 significantly improves the efficiency of the coupling and providing a variety of Dioncophielline and Michellamine analogs in moderate yields.

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Studies of Palladium-Catalyzed Cross-Coupling Reactions for Preparation of Highly Hindered Biaryls Relevant to the Korupensamine/Michellamine Problem

Cited by 72 publications

References 13 publications

Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations

Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations

A Stereospecific, Intermolecular Biaryl-Coupling Approach to Korupensamine A En Route to the Michellamines

Synthetic analogs of dioncophylline and michellamines by stille coupling

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