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

By Li-Xin Dai, Xue-Long Hou

This ebook meets the long-felt want for a reference on ferrocenes with the point of interest on catalysis. It presents an intensive assessment of the synthesis and characterization of other forms of chiral ferrocene ligands, their software to numerous 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 consultant to the layout of latest ferrocene ligands and synthesis of chiral artificial intermediates, and should hence be priceless for natural, catalytic and artificial chemists operating in academia, business study or procedure 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 purposes 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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Additional info for Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications

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Pd(0), ArI Fe 3. R2PCl 44 O Taniaphos 36 (second generation) 2. t-BuLi + S Fe PR2 45 PR2 MOPF 41 t-Bu O PAr2 Fe 2. t-BuLi 3. Ar2PCl 43 1. 10 Representative syntheses of planar chiral ligands 36, 40 and 41 based on ferrocenylsulfoxides 26a,b. with ortho-phosphinylbenzaldehyde to afford diastereomer 43 as the major product. Sequential methylation of the alcohol, sulfoxide-lithium exchange using t-BuLi, and addition of chlorodiarylphosphine produces the second generation Taniaphos ligand 36 in good yield [57].

However, a comprehensive coverage of work regarding the stereoselective induction of planar chirality in ferrocenes is beyond the scope of this chapter. Not covered is, for example, the Schmalz [27] report describing the asymmetric insertion of carbenoids into the CpÀH bond of ferrocene to achieve the enantioselective construction of planar chiral ferrocenes with moderate stereoselectivity. 2 Axial chirality induced upon complexation of a ferrocenyl oxazoline with a metal. 2 Diastereoselective Directed ortho-Metalation of Ferrocenes with Chiral Auxiliaries optically active 1,3-disubstituted [28] and rare multisubstituted planar chiral ferrocenes, are also not presented in this chapter.

R2PCl Ar 1. Pd(0), ArI Fe 3. R2PCl 44 O Taniaphos 36 (second generation) 2. t-BuLi + S Fe PR2 45 PR2 MOPF 41 t-Bu O PAr2 Fe 2. t-BuLi 3. Ar2PCl 43 1. 10 Representative syntheses of planar chiral ligands 36, 40 and 41 based on ferrocenylsulfoxides 26a,b. with ortho-phosphinylbenzaldehyde to afford diastereomer 43 as the major product. Sequential methylation of the alcohol, sulfoxide-lithium exchange using t-BuLi, and addition of chlorodiarylphosphine produces the second generation Taniaphos ligand 36 in good yield [57].

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