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by Siu-leung Ng. / Thesis (M.Phil.)--Chinese University of Hong Kong, 1994. / Includes bibliographical references (leaves 61-62). / Acknowledgments --- p.i / Content --- p.ii / List of Schemes --- p.iii / List of Tables --- p.iv / List of Spectra --- p.v / Abstract --- p.viii / Abbreviations --- p.x / Chapter I. --- Introduction --- p.1 / Chapter II. --- Literature survey / Chapter II.1. --- Ring expansion of cyclic enamines via a [2+2]cycloaddition --- p.4 / Chapter II.2. --- The Ito-Saegusa protocol --- p.6 / Chapter II.3. --- "The Suzuki-Watanabe-Noyori palladium(0)-catalyzed ring opening of cyclic α,β-epoxy ketones" --- p.7 / Chapter III. --- Synthetic plan --- p.9 / Chapter IV. --- Results and discussion / Chapter IV. 1. --- General routes to [n]metacyclophanes (24) and (n+2)- methoxy[n]metacyclophane 35 --- p.15 / Chapter IV.2. --- Birch reduction of 24 and 35 and ozonolvsis of 25 and 36 --- p.17 / Chapter IV.3. --- Synthetic applications / Chapter IV.3.1. --- Synthesis of heterocyclophanes --- p.27 / Chapter IV.3.2. --- Synthesis of exaltone (8) --- p.28 / Chapter V. --- Conclusion --- p.30 / Chapter VI. --- Experimental --- p.31 / Chapter VII. --- References --- p.61 / Chapter VIII. --- 1H and 13C NMR spectra of selected compounds --- p.63

A general straightforward synthetic approach for the enantioselective construction of medium and large ring cyclopropyl ketones via diastereoselective Simmons-Smith cyclopropanation is discussed. Medium and large 2-cycloalkenone 1,4Di-O-benzyl-L-threitol ketals undergo efficient and diastereoselective cyclopropanation when treated with an excess of the Simmons-Smith reagent. The cyclopropyl ketals are obtained in 80-94% with >23:1-8:1 diastereoselectivity. The first enantioselective synthesis of (-)-modhephene, a natural product possessing the carbocyclic (3.3.3) propellane skeleton, by the use of diastereoselective cyclopropanation methodology is described.

Luk To. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2005. / Includes bibliographical references (leaves 115-123). / Abstracts in English and Chinese. / Contents --- p.i / Acknowledgement --- p.ii / Abstract --- p.iii / Abbreviation --- p.vi / Chapter 1. --- Introduction --- p.1 / Chapter 1-1 --- Background --- p.1 / Chapter 1-2 --- Sharpless Epoxidation --- p.2 / Chapter 1-3 --- Mn-Salen Complexes for Epoxidation --- p.4 / Chapter 1-4 --- Oxaziridinium Salts --- p.6 / Chapter 1-5 --- Dioxiranes --- p.9 / Chapter 1-6 --- Asymmetric Epoxidation by Dioxirane --- p.12 / Chapter 2. --- Results and Discussion --- p.31 / Chapter 2-1 --- Epoxidation of trαns-disubstituted and trisubstituted alkenes catalyzed by L-αrαbino-4-uloses --- p.31 / Chapter 2-2 --- Epoxidation of cis-alkenes catalyzed by L-arabino-4-uloses --- p.47 / Chapter 2-3 --- Epoxidation of alkenes catalyzed by new L-arabino-4-uloses --- p.55 / Chapter 3. --- Conclusion --- p.77 / Chapter 4. --- Experimental Section --- p.80 / Chapter 5. --- References --- p.115 / Chapter 6. --- Appendix --- p.124