Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions

Domino Reactions in Organic Synthesis

Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds

Cyclizations of N-acyliminium ions.

The constant pressure to prepare compounds in a more efficient manner has placed the process by which traditional synthetic chemistry is conducted under scrutiny. Areas that have the potential to be improved must be highlighted and modified, so that we can approach the criterion of the 'ideal synthesis'. One area that offers this prospect is the minimization of the use of protecting groups in synthesis. A protection/deprotection event introduces at least two steps into a sequence, incurring costs from additional reagents and waste disposal, and generally leads to a reduced overall yield. Here we present relevant historical context and highlight recent (post-2004) total syntheses that have developed new chemistry in an effort to exclude protecting groups. The invention of chemoselective methodologies is crucial to the execution of 'protecting-group-free' synthesis, and recent advances in this area are also highlighted.

Protecting-group-free synthesis as an opportunity for invention

Die organisch-chemische Synthese hat stets eine grose Faszination auf den Chemiker ausgeubt, und sie wird auch in Zukunft nichts von ihrer Bedeutung verlieren. Es ist eine Binsenweisheit, das alle Chemiker - und nicht nur die - auf die Synthese chemischer Verbindungen, mit denen sie arbeiten wollen, angewiesen sind. So ist die organisch-chemische Synthese heute mehr denn je die Schnittstelle von Organischer Chemie, Biologie. Biochemie, Medizin, Physik und Materialwissenschaft. Man sollte auch nicht vergessen, das die Grundlage der chemischen Industrie die Synthese ist. Fur den Synthetiker aus Leidenschaft aber ist die Synthese weit mehr als nur Mittel zu dem Zweck, Verbindungen in die Hand zu bekommen; sie ist Ausdruck seiner Kreativitat. Intelligenz und seines handwerklichen Konnens, aber auch seiner Ausdauer.

Sequentielle Transformationen in der Organischen Chemie eine Synthesestrategie mit Zukunft

Vinylsilane- and alkynylsilane-terminated cyclization reactions

Total synthesis of (.+-.)-fawcettimine

Preparation of eight-membered cyclic ethers by Lewis acid promoted acetal-alkene cyclizations

Reactions d'aldehydes (phenyl-2 ou benzyloxy-3 propanal par exemple) et d'enones (phenyl-5 hexene-3 one-2) avec des allylsilones (allyl trimethyl- ou methyl-2 allyl trimethyl silane)

Acyclic stereoselection. 22. Diastereofacial selectivity in the Lewis acid mediated reactions of allylsilanes with chiral aldehydes and enones

Synthese d'alkylidene-3 perhydrofurannes, -perhydropyrannes et -oxepannes et de dihydro-5,6 2H-pyrannes par cyclisation acide d'ω-alcoxymethoxyalkyl-1' alcene-1' yl trimethyl silanes

Todd A. Blumenkopf

Papers

Vinylsilane- and alkynylsilane-terminated cyclization reactions

Total synthesis of (.+-.)-fawcettimine

Preparation of eight-membered cyclic ethers by Lewis acid promoted acetal-alkene cyclizations

Acyclic stereoselection. 22. Diastereofacial selectivity in the Lewis acid mediated reactions of allylsilanes with chiral aldehydes and enones

Acetal-initiated cyclizations of vinylsilanes. A general synthesis of allylically unsaturated oxacyclics