By Li-Xin Dai, Xue-Long Hou
This e-book meets the long-felt want for a reference on ferrocenes with the point of interest on catalysis. It offers an intensive evaluation of the synthesis and characterization of other 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 through the "who's who" of ferrocene catalysis, it is a advisor to the layout of recent ferrocene ligands and synthesis of chiral artificial intermediates, and may therefore be necessary for natural, catalytic and artificial chemists operating in academia, business study or method development.Content:
Chapter 1 advent (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 similar 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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Additional info for Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications
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 Ugis chiral amine (N,N-dimethylferrocenylethylamine) almost exclusively.
The lack of a-reactivity of a-ferrocenyl ethers 78 towards alkyllithiums contrasts with the a-deprotonation of benzyl ethers whose consequence is the [1,2]-Wittig rearrangement . 20). Thus, using excess n-BuLi followed by electrophile quench leads, perhaps via the putative dianion intermediate (S,Rp)-86, to products (S,Rp)-87 in good yield and up to 90% de. 2 equiv of n-BuLi in ether at À20 C. 20 Diastereoselective DoM of chiral a-ferrocenyl carbinols. j 2 Stereoselective Synthesis of Planar Chiral Ferrocenes 34 N N N Ph 1.
I-Pr (Sp ) (S) Fe 20 min 3. 2 equiv t-BuLi, –78 °C, 15 min (S)-26b (S,S p)-46 4. 11 The synthesis of the planar chiral (S,Sp)-1,2-disubstituted ferrocene 46. 12). From acetal 48, 2-substituted products 49 may be prepared in high yield and excellent de (98%) via selective lithiation of the prochiral R hydrogen of the Cp ring. In this process, the temperature is crucial for the observed diastereoselectivity; lithiation at 0 C gives products in 80% de. 13) . Notably, Manoury and coworkers reported a highly enantioselective synthesis of 1,2,10 -trisubstituted and 1,2,10 ,20 tetrasubstituted planar chiral ferrocenedicarbaldehydes.
Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications by Li-Xin Dai, Xue-Long Hou