Synfacts 2006(7): 0697-0697  
DOI: 10.1055/s-2006-941923
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Additions of Allyl- and Crotylboronates to Aldehydes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
V. Rauniyar, D. G. Hall*
University of Alberta, Canada
Further Information

Publication History

Publication Date:
22 June 2006 (online)

Significance

The allylation of carbonyls is a very important reaction for the synthesis of useful building blocks. While there are many allylation reagents and protocols, this report provides a broad scope of substrates and provides homoallylic alcohols with high selectivities (high er and dr). The use of the Lewis acid assisted Brønsted acid (LBA) system proved necessary for obtaining a fast and selective reaction. The addition of Na2CO3 was necessary for the scavenging of HCl (from SnCl4).