A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar:  Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

Liu, Duan; Li, Wenge; Zhang, Xumu

doi:10.1021/ol0269998

Cited by 57 publications

(23 citation statements)

References 19 publications

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“…However, only 27% overall yield (97% ee) was obtained for this chiral inhibitor via a traditional resolution procedure and the work up is very difficult to handle. Zhang reported the synthesis of a new C 2 -symmetrical chiral ferrocenyl polysubstituted phospholane ligand L-8 (Scheme 7.11), which was obtained with a similar procedure as that for FerroTANE [28]. Thus, the key intermediate 1,4-diol cyclic sulfate 27 was prepared from D-mannitol 24 in three steps, with 25 and 26 as intermediates, in an overall yield of 20%.…”

Section: C-centered Chiral Diphosphine Ligandsmentioning

confidence: 99%

Symmetrical 1,1′‐Bidentate Ferrocenyl Ligands

Zhang

Liu

2009

Chiral Ferrocenes in Asymmetric Catalysis

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Section: C-centered Chiral Diphosphine Ligandsmentioning

confidence: 99%

Symmetrical 1,1′‐Bidentate Ferrocenyl Ligands

Zhang

Liu

2009

Chiral Ferrocenes in Asymmetric Catalysis

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“…5) have recently been described and tested, with sometimes quite impressive results. Interesting examples are f-binaphane [11], ferrotane [12], L2 with only planar chirality [13], bisphosphonite L3 [14], the sugar-based phospholane L4 [15] and the P-chiral phosphines L5 [16]. Rh complexes of ferrotanes showed very good performance for various amido itaconates, and achieved very high TONs and TOFs for substrate 4 (Table 25.3, entry 3.1).…”

Section: Miscellaneous Diphosphinesmentioning

confidence: 99%

Enantioselective Hydrogenation of Alkenes with Ferrocene‐Based Ligands

Blaser¹,

Lotz²,

Spindler³

2006

The Handbook of Homogeneous Hydrogenation

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IntroductionFerrocene as a (at the time rather exotic) backbone for chiral ligands was introduced by Kumada and Hayashi [1] based on Ugi's pioneering studies related to the synthesis of enantiopure ferrocenes ( Fig. 25.1). Ppfa, as well as bppfa and bppfoh, proved to be effective ligands for a variety of asymmetric transformations. From this starting point, several ligand families with a range of structural variations have been developed during the past few years. In this chapter we will describe effective ligand structures developed over time, the main focus being on diphosphine derivatives ( Fig. 25.2) and their application to the hydrogenation of alkenes. Three recently published reviews cover some of the same area, but from slightly different points of view. Colacot and Barbaro et al. [2] presented general overviews on ferrocene-based chiral ligands and their application to various asymmetric transformations, while Blaser et al. [3] and Tang and Zhang [4] reviewed the recent progress in the application of diphosphines for the enantioselective hydrogenation. These reviews can serve to put the present account into a broader perspective.This chapter is organized according to the position of the phosphine groups P, as depicted in Fig. 25.2. It is important to realize that many of the ligands described here have both planar (C p ring with two different substituents) as well 833 The Handbook of Homogeneous Hydrogenation. Edited by J. G. de Vries and C. J. ElsevierFig. 25.1 Structures of Ugi's amine and the first ferrocene-based chiral phosphine ligands.

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“…Their syntheses and their applications have been widely studied [60]. Now, combinations of ferrocene derivatives with Pd, Cr and other ions have been frequently used in the hydrosilylation of norbornene [61], addition of diethylzinc to aldehydes [62], and so on [77b, 45,87,97].…”

Section: Organo-fe Complexesmentioning

confidence: 99%

“…The chiral catalyst 147 derived from a sugar promoted conversations of α-dehydroamino acid compounds to the corresponding amides in up to 99%ee [97]. Zhang and coworkers showed that hydrogenation conversions of different aliphatic and aromatic substrate were close to 100% and most enantioselectivities were over 99%.…”

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confidence: 99%

Recently Developed Organometallic Complexes of Zn, Cu(Zn, Li), Fe, Ru and Less-used Ions. Use in Selective 1,2-or 1,4-Additions, Transfer Hydrogenations, Aldol Reactions and Diels-Alder Reactions

Zhu¹,

Jiang

Ren

et al. 2005

COS

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This review introduces the broad general topic of asymmetric organic synthetic reactions and reagents. Reagents containing both frequently used metallic ions, e.g. Zn ++ , Cu +(++) and Ru ++ , and rarely used ions, such as Ag + , employed in the construction of designed chiral centers, are updated here. Enantioselective 1,2-additions and 1,4-conjugate additions, transfer hydrogenations, and diasteroselective aldol reaction are discussed. The selectivities induced by chiral β-, δor γ-chiral amino alcohols, chiral diols, chiral binaphthyl derivatives, chiral P,N-containing auxiliaries, and other ligands used to prepare chiral metallic complexes, were compared in each reaction system. The use of two or more metallic ions with a single chiral ligand has now become a more popular strategy to catalyze chiral-center-controlled processes. For example, only diethylzinc was used in enantioselective additions to aldehydes in early studies. Recently, the combination of Et 2 Zn and Cu ++ in the selective additions has been used to achieve high ee% values and yields. Finally, quantum calculations have been used to obtain kinetic data to predict a reactions ee% values. For example, the calculated ∆G cal. values have a strong relationship with the obtained ∆G fit values which have the direct linkage with the ee% values. EntryActivator ee (%) at 0 °°°°C (config.) ee (%) at -45 °°°°C (config.)

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A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar: Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

Cited by 57 publications

References 19 publications

Symmetrical 1,1′‐Bidentate Ferrocenyl Ligands

Symmetrical 1,1′‐Bidentate Ferrocenyl Ligands

Enantioselective Hydrogenation of Alkenes with Ferrocene‐Based Ligands

Recently Developed Organometallic Complexes of Zn, Cu(Zn, Li), Fe, Ru and Less-used Ions. Use in Selective 1,2-or 1,4-Additions, Transfer Hydrogenations, Aldol Reactions and Diels-Alder Reactions

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