Topological Strategies: Sigmatropic Rearrangements

Topological Strategies: Sigmatropic Rearrangements -...

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Me O O O O O H Me O H CO 2 H O H 3 CO 2 R' n HO O OTMS O OH O O O O O O CO 2 H HO Me Me OH Me Et O O Me H O Et H Me OH Et O O O O R R' HO 2 C R R' O O R R' HO 2 C R R' Shair Chem 215 Lecture 6: Topological Strategies: Sigmatropic Rearrangements Wednesday, October 3, 2007 Reading Assignment: "The Thermal, Aliphatic Claisen Rearrangement" Ziegler, F. E. Chem. Rev. 1988 , 88 , 1423-1452. "The Ireland-Claisen Rearrangement" Pereia, S.; Srebnik, M. Aldrichimica Acta 1993 , 26 , 17-29. SANROS pp 56-57, 108-109, 294-295, 500-501. Partial List of Topics Discussed: Topological Strategies-Transforms Involving Sigmatropic Rearrangements, Stereochemical Strategies Continued: Asymmetric Catalysis and Kinetic Resolution, Use of Chiral Controller Groups for Absolute Stereochemical Control Partial List of Transforms Covered: Cope Rearrangement Oxy-Cope Rearrangement (Oxy Anion Accelerated Cope Rearrangement) Dieckman Condensation Rubottom Oxidation Selenenylation/Elimination of Unhindered Alcohols
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Unformatted text preview: Nucleophilic Epoxidation Claisen Rearrangement Ireland Ester Enolate Claisen Rearrangement References: (+)-CP-263,114: Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000 , 122 , 7424-7425. Periplanone B: Still, W. C. 1979 , 101 , 2493-2495. Schreiber, S. L.; Santini, C. 1984 , 106 , 4038-4039. Lasalocid A: Ireland, R. E.; Anderson, R. C.; Badoud, R.; Fitzsimmons, B. J.; McGrarvey, G. J.; Thaisrivongs, S.; Wilcox, C. S. 1983 , 105 , 1988-2006. Ireland, R. E.; Thaisrivongs, S.; Wilcox, C. S. 1980 , 102 , 1155-1157. Syntheses Discussed: Graphical Transform Guide: ()-Periplanone B ()-CP-263,114 Lasalocid A R O OH X X R HO O n Me Me...
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