ChemInform Abstract: A New Stereocontrolled Synthesis of the Racemic Forms of Savinin and Gadain.

Rossi, Renzo; Bellina, Fabio; Bechini, Chiara; Mannina, Luisa

doi:10.1002/chin.199802238

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“…In addition to the alkyne elementometalation routes to type V−VIII alkenyl derivatives, some highly selective alkyne polar addition routes to type V−VIII alkenyl derivatives, such as xviii , xix , xxiii , and xxv shown in Scheme , along with many other type III and IV alkenyl derivatives, have been shown to be synthetically useful, and their applications are shown throughout this paper. Applications of some of the less widely used ones are summarized in Scheme …”

Section: Highly (≥98%) Selective and Efficient Syntheses Of Dienes En...mentioning

confidence: 99%

Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

et al. 2010

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Palladium-catalyzed cross-coupling reactions, especially those involving Zn, Al, Zr (Negishi coupling) and B (Suzuki coupling), collectively have brought about "revolutionary" changes in organic synthesis. Thus, two regio-and stereodefined carbon groups generated as R 1 M (M = Zn, Al, B, Cu, Zr, etc.) and R 2 X (X = I, Br, OTs, etc.) may now be cross-coupled to give R 1 -R 2 with essentially full retention of all structural features. For alkene syntheses, alkyne elementometalation reactions including hydrometalation (B, Al, Zr, etc.), carbometalation (Cu, Al-Zr, etc.), and haloboration (BX 3 where X is Cl, Br, and I) have proven to be critically important. Some representative examples of highly efficient and selective (≥98%) syntheses of di-, tri-and oligoenes containing regio-and stereodefined di-and trisubstituted alkenes of all conceivable types will be discussed with emphasis on those of natural products. Some interesting but undesirable cases involving loss of the initial structural identities of the alkenyl groups are attributable to the formation of allylpalladium species, which must be either tamed or avoided. Some such examples involving the synthesis of 1,3-, 1,4-, and 1,5-dienes will also be discussed.

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Section: Highly (≥98%) Selective and Efficient Syntheses Of Dienes En...mentioning

confidence: 99%

Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

et al. 2010

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show abstract

ChemInform Abstract: A New Stereocontrolled Synthesis of the Racemic Forms of Savinin and Gadain.

Cited by 1 publication

References 1 publication

Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

Alkyne Elementometalation−Pd-Catalyzed Cross-Coupling. Toward Synthesis of All Conceivable Types of Acyclic Alkenes in High Yields, Efficiently, Selectively, Economically, and Safely: “Green” Way

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