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Synthesis of Cyclic Fragrances via Transformations of Alkenes,Alkynes and Enynes: Strategies and Recent Progress
Authors:Zhigeng Lin  Baoying Huang  Lufeng Ouyang  Liyao Zheng
Institution:School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China; (Z.L.); (B.H.); (L.O.)
Abstract:With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.
Keywords:cyclization  cycloaddition  carbocycles  heterocycles  unsaturated hydrocarbons  natural fragrances  synthetic odorants  transition-metal catalysis  asymmetric organocatalysis  cascade/tandem/domino reaction
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