有机合成方法(研究生用)_C-C formation.ppt

Peterson Olefination Tebbe and Petasis Reagents Tebbe Reagents Tebbe Reagents McMurry Coupling Furstner : Goes further with McMurry Coupling Deoxygenation Reactions Shapiro Reaction 双键顺反的控制 Synthesis of Tetrasubstituted Alkenes by Stereo- and Regioselective Stannyllithiation of Diarylacetylenes J. Am. Chem. Soc., 2010, 132 (34), pp 11854–11855 双键顺反的控制问题 3. Fritsch-Buttenberg-Wiechell (FBW) Rearrangement J. Am. Chem. Soc. 2000, 122, 10736-10737 Prepare Polyynes Mitsunobu Reaction Mechanism of the Mitsunobu Reaction J. Org. Chem. 2005, 70, 8385-8394. Org. Lett. 2005, 7, 4573-4576 Org. Lett. 2000, 2, 1637 Balz-Schiemann Reaction (Aromatic Fluorination-1) Stefan Braese, Angew. Chem. Int. Ed. 2010, 49, 5986 –5988 Aromatic Fluorination-2 DOI: 10.1002/anie.200905052 J. AM. CHEM. SOC. 2004, 126, 5352-5353 Quiz?? Answer C. Chem, M. E. Layton, S. M. Sheehan, M. D. Shair, J. Am. Chem. Soc. 2000, 122, 7424; (b) C. Chem, M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784. Oxidative Enolate Coupling (1) OS, 2008, 158 Oxidative Enolate Coupling (baran’s work) 1. ACIE, 2005, 44, 609; 2. JACS, 2004, 126, 7450; 3. Accounts, 2009, 530; ……. Oxidative Enolate Coupling in Total Synthesis (Baran’s Work) Oxidative Enolate Coupling (Dawei Ma’s work) Dawe Ma, JACS, 2010 2. Organometallic Reagents 金属锂试剂 Li-Halogen exchange Li-Halogen exchange Li-Halogen exchange Li-Halogen exchange Directed Ortho Metalation With Lithium Reagents Directed Ortho Metalation With Lithium Reagents Directed Ortho Metalation With Lithium Reagents Directed Ortho Metalation With Lithium Reagents Ref: 1) Aggarwal, V. K. et al, Nature, 2008, 456, 778-782 2) Aggarwal, V. K. et al, angew. chem. Int. Ed. 2007, 46, 7491 Directed Ortho Metalation With Lithium Reagents Aziridinyl Anions: Generation, Reactivity, and Use in Modern Synthetic Chemistry, Chem. Rev. 2010 Directed Ortho Metalation With Lithium Reagents Grignard Reagents Paul Knochel (LMU) Synthesis of Ortho-Nitro-Functionalized Grignard Reag