NOBIN-based phosphoramidite and phosphorodiamiditeligands and their use in asymmetric nickel-catalysed hydrovinylation

文献情報

出版日 2012-11-01

DOI 10.1039/C2CY20657A

インパクトファクター 6.119

著者

Mike Schmitkamp, Walter Leitner, Giancarlo Franciò

原文を見る

要旨

Phosphoramidite and P-stereogenic phosphorodiamidite ligands derived from (Sa)-2-phenylamino-2′-hydroxy-1,1′-binaphthyl (N-Ph-NOBIN) and bis(1-phenyl-ethyl)amine were synthesised, fully characterised, and the absolute configuration of the stereogenic phosphorus atoms was assigned. The phosphoramidite ligand L2 features three non-bridged substituents at phosphorus comprising the bis(1-phenylethyl)amine and two NOBIN moieties. The NOBIN units are bound to the phosphorus through the oxygen atoms with two pendant nitrogen atoms. In the Ni-catalysed hydrovinylation of styrene no conversion was observed with the phosphorodiamidites, while the phosphoramidite ligands led to active catalysts with a marked co-operative effect on selectivities. Whereas the racemic product was obtained with the (Sa,Sa,SC,SC) diastereomer, the (Sa,Sa,RC,RC) diastereomer proved to be one of the best ligands for this reaction, leading to almost perfect selectivity and ees of up to 91%.

掲載誌

Catalysis Science & Technology

CiteScore: 5.91

自己引用率: 4.5%

年間論文数: 600

Catalysis Science & Technology is committed to publishing research reporting high-quality, cutting-edge developments across the catalysis community at large. The journal places equal focus on publications from the heterogeneous, homogeneous, thermo-, electro-, photo-, organo- and biocatalysis communities. Works published in the journal feature a balanced mix of fundamental, technology-oriented, experimental, computational, digital and data-driven original research, thus appealing to catalysis practitioners in both academic and industrial environments. Original research articles published in the journal must demonstrate new catalytic discoveries and/or methodological advances that represent a significant advance on previously published work, from the molecular to the process scales. We welcome rigorous research in a wide range of timely or emerging applications related to the environment, health, energy and materials. Catalysis Science & Technology publishes Communications, Articles, Reviews and Perspectives. More details regarding manuscript types may be found in the Information for Authors section.

NOBIN-based phosphoramidite and phosphorodiamiditeligands and their use in asymmetric nickel-catalysed hydrovinylation

文献情報

おすすめジャーナル

関連文献

A novel layered oxysulfide intergrowth compound Sr4Mn2Cu5O4S5 containing a fragment of the α-Cu2S antifluorite structure

Secondary nucleation of the β-polymorph of l-glutamic acid on the surface of α-form crystals

Dioxygen activation by a dinuclear nickel thiolate complex: structural characterization of the ligand oxidized product

Charge transfers influence on the spin ground state of manganese and iron superoxide dismutases: a DFT study on a model of the reduced active site interacting with O2−

N–PtIV–H/N–H⋯PtII intramolecular redox equilibrium in a product of H–C(sp2) cleavage and unusual alkane/arene C–H bond selectivity of ([2.1.1]pyridinophane)PtII(CH3)+

Three-fold interpenetrating three-dimensional networks based on C-methylcalix[4]resorcinarene incorporating benzophenone guest molecules

The reaction of phenyldimethylsilyllithium with N-phenylpyrrolidone

Synthesis and characterization of highly ordered mesoporous thin films with –COOH terminated pore surfaces

Polymorphism of pure p-tert-butylcalix[4]arene: conclusive identification of the phase obtained by desolvation

Catalytic insertion of diazo compounds into N–H bonds: the copper alternative

こちらもおすすめ

環戊烷-1,3-二甲酸甲酯はどのように合成されますか？

4-メトキシ-1,2,3-スチアゼ-3,5-ジオンとは何ですか？

プロスタグランジンA2について「に適用される法規ガイドラインは何ですか？'

4-アミノ-1-ナフタレン sulfonic 酸についての物理化学的性質は何ですか？

N-GlcNAc-生物素を取り扱う際の実験室安全事項は何ですか？

3-アミノメチルフローラノピペリジン-1-カルボニル酸テルブチルエステルとは何ですか？

6-溴-1-甲基-1H-ベンゾ[d][1,2,3]三氮唑はどのように合成されますか？

4-硫代尿苷はどのように合成されますか？

ブレインナトリユリックペプチド32ラットとは何ですか？

1-(3-氮杂啶)-4-羟基哌啶双盐酸盐の物理化学的性質は何ですか？

掲載誌

Catalysis Science & Technology

おすすめ化合物

2,5-Dichloro-3-methylthiophene

5,7,8'-Trihydroxy-2',2'-dimethyl-2'H,4H-3,6'-bichromen-4-one

2-Nitrobenzotrifluoride

Atosiban Acetate

2-Methyl-2-propanyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate

おすすめサプライヤー