One or More CH, CC, and/or C C Bond(s) Formed by Rearrangement

作者: M.T. Molina , J.L. Marco-Contelles

DOI: 10.1016/B0-08-044655-8/00018-0

关键词: Claisen rearrangementEnantioselective synthesisHeteroatomCyclopropaneStereochemistrySigmatropic reactionCatalysisDouble bondCope rearrangementChemistry

摘要: This chapter reviews rearrangement reactions that form a double bond and the period covered is 1995–2003. The discussed have broad scope and, although major emphasis given to synthetic aspects, especially in area of natural products synthesis, mechanistic (and computational calculations) stereochemical features (including asymmetric catalysis) are also mentioned. The first section deals with hydrogen migration different orders, [1,2]- [1, j ]-, including sigmatropic, acid-, base-, metal-catalyzed migrations hydrogen. In second section, [1, j]-rearrangements involving C-migration collected, sigmatropic vinylcyclopropanes vinylcyclobutanes. The [3,3]-sigmatropic rearrangements comprising Cope rearrangement, its variants, thermal, photochemical, catalyzed, examined. heteroatom versions: oxy-Cope anionic oxy-Cope), aza-Cope, oxonia-Cope included. Claisen variants: Ireland–Claisen, Johnson–Claisen, Eschenmoser–Claisen, Carroll, thia-Claisen, aza-Claisen been final provides information about tandem higher rearrangements, cyclopropane ring-opening epoxide rearrangements.

参考文章(1,331)
Sharad K. Verma, Everly B. Fleischer, Harold W. Moore, Synthesis of Angular Triquinanes from 1-Alkynylbicyclo[3.2.0]hept-2-en-7-ones. A Tandem Alkoxy-Cope Ring Expansion/Transannular Ring Closure Reaction Journal of Organic Chemistry. ,vol. 65, pp. 8564- 8573 ,(2000) , 10.1021/JO0009503
Wing-Yan Tsui, Geoffrey Brown, Acid-catalysed rearrangement of caryophyllene oxide Journal of The Chemical Society-perkin Transactions 1. pp. 2507- 2509 ,(1996) , 10.1039/P19960002507
Noritaka Chida, Kohji Sugihara, Seiji Amano, Seiichiro Ogawa, Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose Journal of The Chemical Society-perkin Transactions 1. pp. 275- 280 ,(1997) , 10.1039/A604365H
Simona Ceccarelli, Umberto Piarulli, Cesare Gennari, Synthetic studies on sarcodictyins and eleutherobin: Synthesis of fully functionalized cyclization precursors Tetrahedron Letters. ,vol. 40, pp. 153- 156 ,(1999) , 10.1016/S0040-4039(98)80045-2
Kevin Blades, Sunita T Patel, Jonathan M Percy, Robin D Wilkes, Facile [2,3]-rearrangements of difluoroallylic alcohols with CP and CS bond formation Tetrahedron Letters. ,vol. 37, pp. 6403- 6406 ,(1996) , 10.1016/0040-4039(96)01358-5
Joji Ohshita, Kazuhiro Yoshimoto, Toshiyuki Iida, Atsutaka Kunai, Oxa-Cope Rearrangement of Silenes Thermally Generated from 1,2-Bis[tris(trimethylsilyl)silylcarbonyl]alkanes Journal of the American Chemical Society. ,vol. 123, pp. 8400- 8401 ,(2001) , 10.1021/JA0109646
Gerald Pattenden, Allison J. Smithies, Concise syntheses of cembrenes based on radical-mediated vinylcyclopropane ring-opening reactions in casbene Journal of The Chemical Society-perkin Transactions 1. pp. 57- 61 ,(1996) , 10.1039/P19960000057
Michail N Elinson, Sergey K Feducovich, Gennady I Nikishin, Electrochemically induced oxidative rearrangement of alkylidenemalonates Tetrahedron. ,vol. 54, pp. 14529- 14540 ,(1998) , 10.1016/S0040-4020(98)00912-0
Mariella Mella, Mauro Freccero, Angelo Albini, Characterization of Methylenepropenylidenecyclohexadiene Derivatives and Their Competing 1,6-Electrocyclic Reaction and 1,7-Hydrogen Shift at Room Temperature Journal of the American Chemical Society. ,vol. 118, pp. 10311- 10312 ,(1996) , 10.1021/JA9621455