New Classical Propargylic Rearrangements in Natural Products Synthesis: Rearrangements of propargylic alcohols and propargylic esters - Couverture souple

MARCO-CONTELLES, JOSÉ; Do Carmo Carreiras, Maria

 
9783843353281: New Classical Propargylic Rearrangements in Natural Products Synthesis: Rearrangements of propargylic alcohols and propargylic esters
Couverture souple
ISBN 10 : 384335328X ISBN 13 : 9783843353281
Editeur : LAP LAMBERT Academic Publishing, 2010

Synopsis

In this book we highlight the strong synthetic potential and scope of transition metal-catalyzed rearrangement reactions for fully economical and complex carbon-carbon bond forming reactions. The Meyer-Schuster and the Rupe rearrangements are emerging as the methods of choice for the homologation of carbonyl compounds into ?,?-unsaturated aldehydes and ketones, particularly useful for the synthesis of many hindered ketones. The Rautenstrauch-I and Rautenstrauch-II rearrangements of readily propargylic derivatives are very useful reactions for the synthesis of complex cyclopentenones, and bicyclo[n.1.0] enol carboxylates in high chemical yields, which proceed under mild reaction conditions with high stereoselectivity, and total transfer of chirality. In the case of Rautenstrauch-II, the basic-methanolysis of the resulting compounds provides bicyclo[n.1.0]ketones, valuable building blocks for the preparation of natural products. A reaction mechanism has been advanced, and confirmed by experimental evidences, which supports the involvement of metallo-carbenes as key species formed through a cyclopropanation event that precedes the 1,2-acyloxy migration.

Les informations fournies dans la section « Synopsis » peuvent faire référence à une autre édition de ce titre.

Présentation de l'éditeur

In this book we highlight the strong synthetic potential and scope of transition metal-catalyzed rearrangement reactions for fully economical and complex carbon-carbon bond forming reactions. The Meyer-Schuster and the Rupe rearrangements are emerging as the methods of choice for the homologation of carbonyl compounds into ?,?-unsaturated aldehydes and ketones, particularly useful for the synthesis of many hindered ketones. The Rautenstrauch-I and Rautenstrauch-II rearrangements of readily propargylic derivatives are very useful reactions for the synthesis of complex cyclopentenones, and bicyclo[n.1.0] enol carboxylates in high chemical yields, which proceed under mild reaction conditions with high stereoselectivity, and total transfer of chirality. In the case of Rautenstrauch-II, the basic-methanolysis of the resulting compounds provides bicyclo[n.1.0]ketones, valuable building blocks for the preparation of natural products. A reaction mechanism has been advanced, and confirmed by experimental evidences, which supports the involvement of metallo-carbenes as key species formed through a cyclopropanation event that precedes the 1,2-acyloxy migration.

Biographie de l'auteur

J Marco-Contelles is Senior Research Professor in CSIC, Madrid since 2004. He has developed synthetic methodologies in sugar-nucleoside, free radical and organometallic chemistry (Pauson-Khand, RCM reactions, PtCl2-mediated cycloisomerizations, heterocyclic systems). In 2002 he was bestowed the French-Spanish award of the French Chemical Society.

Les informations fournies dans la section « A propos du livre » peuvent faire référence à une autre édition de ce titre.

Éditeur
LAP LAMBERT Academic Publishing
Date d'édition
2010
Langue
anglais
ISBN 10 
384335328X
ISBN 13 
9783843353281
Reliure
Broché
Nombre de pages
60
Coordonnées du fabricant
non disponible
Personne responsable
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