Synthesizing_Allenes_Today(1982-2006).pdfVIP

REVIEW 795 Synthesizing Allenes Today (1982–2006) Synthesizing Allenes Today (1982–2006)Kay M. Brummond,* Jolie E. DeForrest Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, USA Fax +1(412)6248611; E-mail: kbrummon@pitt.edu Received 14 December 2006; revised 17 January 2007 1 Introduction Abstract: Allenes have allowed chemists to access a variety of structurally interesting and biologically active products. The emer- gence of these unique compounds in organic synthesis is a direct re- Allenes have allowed chemists to access a variety of struc- sult of the discovery and development of efficient protocols for their turally interesting and biologically active products.1–18 The preparation. Moreover, efficient syntheses of the allenyl functional- emergence of these unique compounds in organic synthe- ity are important to the synthetic community and will be reported sis is a direct result of the discovery and development of and discussed in this review. efficient protocols for their preparation. Allenes can be 1 Introduction obtained through a variety of synthetic methods, however 2 Synthesis of Allenes with Aluminum Hydride Reagents this review focuses only on new developments or those 2.1 Allenes from Propargyl Electrophiles not covered in previous reviews. 2.2 Allenes from Enynes 3 Allene Synthesis via Skeletal Rearrangement Reactions Th