Download e-book for iPad: Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and by Li-Xin Dai, Xue-Long Hou

By Li-Xin Dai, Xue-Long Hou

ISBN-10: 3527322809

ISBN-13: 9783527322800

ISBN-10: 3527628843

ISBN-13: 9783527628841

This ebook meets the long-felt desire for a reference on ferrocenes with the point of interest on catalysis. It presents an intensive review of the synthesis and characterization of alternative varieties of chiral ferrocene ligands, their software to varied catalytic uneven reactions, and flexible chiral fabrics in addition to drug intermediates synthesized from them. Written by means of the "who's who" of ferrocene catalysis, it is a advisor to the layout of latest ferrocene ligands and synthesis of chiral artificial intermediates, and may hence be beneficial for natural, catalytic and artificial chemists operating in academia, commercial examine or procedure development.Content:
Chapter 1 creation (pages 1–13): Prof. Dr. Li?Xin Dai and Prof. Dr. Xue?Long Hou
Chapter 2 Stereoselective Synthesis of Planar Chiral Ferrocenes (pages 15–53): Wei?Ping Deng, Victor Snieckus and Costa Metallinos
Chapter three Monodentate Chiral Ferrocenyl Ligands (pages 55–71): Ji?Bao Xia, Timothy F. Jamison and Shu?Li You
Chapter four Bidentate 1,2?Ferrocenyl Diphosphine Ligands (pages 73–95): Hans?Ulrich Blaser and Matthias Lotz
Chapter five 1,2?P,N?Bidentate Ferrocenyl Ligands (pages 97–147): Yong Gui Zhou and Prof. Dr. Xue lengthy Hou
Chapter 6 N,O?Bidentate Ferrocenyl Ligands (pages 149–174): Anne Nijs, Olga Garcia Mancheno and Carsten Bolm
Chapter 7 Symmetrical 1,1??Bidentate Ferrocenyl Ligands (pages 175–214): Wanbin Zhang and Delong Liu
Chapter eight Unsymmetrical 1,1??Bidentate Ferrocenyl Ligands (pages 215–256): Shu?Li You
Chapter nine Sulfur? and Selenium?Containing Ferrocenyl Ligands (pages 257–282): Juan C. Carretero, Javier Adrio and Marta Rodriguez Rivero
Chapter 10 Biferrocene Ligands (pages 283–305): Ryoichi Kuwano
Chapter eleven functions of Aza? and Phosphaferrocenes and comparable Compounds in uneven Catalysis (pages 307–335): Nicolas Marion and Gregory C. Fu
Chapter 12 Metallocyclic Ferrocenyl Ligands (pages 337–368): Christopher J. Richards

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Extra info for Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications

Sample text

1 Methods for the introduction of planar chirality into the ferrocene skeleton. of a racemic mixture with an enzyme gives the corresponding enantiomerically enriched product, while its antipode remains untouched and can be isolated, also in optically active form. Non-enzymatic kinetic resolution is the most recent development in this area. Of the three methods above, type (a) is the most developed and is extensively exploited. Much of the early research on ferrocene-based ligands and reagents for asymmetric catalysis utilized Ugi’s chiral amine (N,N-dimethylferrocenylethylamine) almost exclusively.

Preferential conformation of the sulfoxide moiety during lithiation such that the bulky t-Bu or p-Tol groups are positioned anti to the ferrocene core. The ability to convert the sulfoxide moiety to other functional groups confers a large degree of flexibilty to this method [55], similar to the SN1 substitution reactions available for Ugi’s amine. 9, the p-Tol sulfoxide 31 undergoes sulfur-lithium exchange with t-BuLi [49] or PhLi [50] to give the putative intermediate 32 which may be trapped with various electrophiles to produce a series of 1,2-disubstituted ferrocenes 33 featuring, in many cases, exclusively planar chirality.

MeI Me N Fe Me + 90a 88 N 89 Ph 1. base, THF, –78 °C 2. 21 Diastereoselective ortho-lithiation of ferrocenylimidazolines 88 and 89. above (78), a comparison of metalation of 85 (R ¼ Ph) can be made with DoM of benzyl alcohol, which occurs under rather special conditions [85]. Epimeric ferrocenylimidazolines 88 and 89 were recently shown by Peters [23] to participate in diastereoselective DoM reactions. Interestingly, the relative stereochemistry of the lithiation step is highly dependent upon the nature of the base.

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Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications by Li-Xin Dai, Xue-Long Hou


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