Synthesis 2011(12): 1865-1879  
DOI: 10.1055/s-0030-1260602
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Isothiourea-Catalyzed Asymmetric O- to C-Carboxyl Transfer of Furanyl Carbonates

Caroline Joannesse, Louis C. Morrill, Craig D. Campbell, Alexandra M. Z. Slawin, Andrew D. Smith*
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, UK
Fax: +44(1334)463806; e-Mail: ads10@st-andrews.ac.uk;
Further Information

Publication History

Received 28 April 2011
Publication Date:
25 May 2011 (eFirst)

Abstract

The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the α-regioisomers (α/γ up to 83:17) with high asymmetric induction (up to 83% ee).