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Topological Strategies: Connective Transforms

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Shair Chem 215 Lecture 5: Topological Strategies: Connective Transforms Monday, October 1, 2007 Reading Assignment: "Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts" Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl . 1998 , 37 , 1986-2012. Handouts: Asymmetric Alkylation of Enolates and Asymmetric Allylation Reactions SANROS pp 88-91, 98-99, 138-139, 324-325, 388-389. Partial List of Topics Discussed: Topological Strategies- The Power of Connective Transforms in Synthetic Simplification, An Introduction to Stereochemical Strategies, The Use of Chiral Auxiliaries for Stereochemical Control. Partial List of Transforms Covered: Alkylation of Cyclopentadienyl Anion Curtius Rearrangement Baeyer-Villager Oxidation Iodolactonization Radical Dehalogenation Enamine Alkylation/Robinson Annulation Conjugate Addition (Conjugate Addition of Cuprates) Addition of Organometallic Reagents to Carbonyl Compounds Rhodium(III) Catalyzed Olefin Isomerization Grob Fragmentation
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Unformatted text preview: Photochemical Isomerization of Verbenone α-Alkylation of Extended Enolates Hydroxylation of Enolates Tandem Michael/Aldol Reaction de Mayo Reaction References: Saudin: Winkler, J. D.; Doherty, E. M. J. Am. Chem. Soc . 1999 , 121 , 7425-7426. Taxol: Wender, P. A.; et al. . 1997 , 119 , 2755-2756. Wender, P. A.; et al. . 1997 , , 2757-2758. Prostaglandin F 2 α : Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. H. . 1969 , 91 , 5675-5677. Syntheses Discussed: Graphical Transform Guide: O AcO O OMe Corey Lactone O O Me O N H Ph O O Ph HO Me AcO Me OH OH BzO H AcO H Me Taxol R R N H O OR' RCO 2 H R OR' O R R' O O R CO 2 H I R O n n H X R H O N O R R O R' R O R'M HO R O RM R R' R" R R' R" O OH X O H 3 C CH 3 CH 3 O H 3 C H 3 C CH 3 R O R" R' R O R' R"M R O OH R' R O R' O O O O O O Me H Me Me Saudin O R O HO R 2 R 1 R 4 R 3 R 2 O R 1 R 4(3) O R R 3(4)...
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