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ChemInform Abstract: The Double Annulation of Tethered Diacids and Alkynones: History and Scope
Abstract
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Reviews are listed in order of appearance in the sources indicated. In multidisciplinary review journals, only those reviews which fall within the scope of this Journal are included. Sources are listed alphabetically in three categories: regularly issued review journals and series volumes, contributed volumes, and other monographs. Titles are numbered serially, and these numbers are used for reference in the index. Major English-language sources of critical reviews are covered. Encyclopedic treatises, annual surveys such as Specialist Periodical Reports, and compilations of symposia proceedings are omitted. This installment of Recent Reviews covers principally the early part of the 2001 literature. Previous installment: J. Org. Chem. 2001, 66(7), 2538-46.
The double Michael reaction of a tethered carbon diacid (a 1,n-dinucleophile) with an alkynone (a 1,1-dielectrophile) provides highly substituted and functionalized monocyclic double Michael adducts in what is formally an [n+1] annulation. The pendant functionality in the double Michael adduct can be used to effect a second annulation. A history and overview of the "double annulation" route to bicyclic compounds is presented. The scope and selectivity of the route is also discussed. 1. Genesis of the idea 2. Exodus - time in the wasteland and ultimate redemption 3. Leviticus - laws governing the double Michael reaction 4. Numbers - diverse bicyclic compounds derived from the double Michael adducts 5. Deuteronomy - historical context and outlook.