Synthesis of Optically Active Bifunctional Building Blocks through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

Link: http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/asap/abs/jo0625655.html

From Prof. Ben L. Feringa's group at University of Groningen, The Netherlands

A nice copper catalyzed method for enatioselective SN2' displacement of allyl bromide with Grignard reagents using ferrocene-based ligand was recently published in JOC ASAP. Note that the b/l ratio seen in the table indicates the branch/linear ratio of products.
Three substrates 1a, 1b, 1c were chosen to show the compatability of the protected hydroxyl and amino groups under the reaction conditions. All figures were taken directly from their paper.
Subsequent transformations of the products 2a and 2b were also presented to demonstrate the utilities of their method.

For product 2a

For product 2b

Product 2b was also used to show that chiral beta-amino acid can be synthesized from it.