ChemInform Abstract: Silyl Fluoride Electrophiles for the Enantioselective Synthesis of Silylated Pyrrolidine Catalysts.

Abstract

Silyl Fluoride Electrophiles for the Enantioselective Synthesis of Silylated Pyrrolidine Catalysts. -(-)-Sparteine-mediated treatment of the pyrrole (I) with the silyl fluorides (II) allows efficient and highly stereoselective access to the products (III). The latter can smoothly be converted into enantiopure pyrroles by recrystallization or trituration. The derivative (IVa) and the free amine (SIL) efficiently promote the asymmetric Michael addition of aldehydes to nitrostyrenes. -(JENTZSCH, K. I.; MIN, T.; ETCHESON, J. I.; FETTINGER, J. C.; FRANZ*, A. K.; J. Org. Chem. 76 (2011) 17, 7065-7075, http://dx.doi.org/10.1021/jo200991q ; Dep. Chem., Univ. Calif., Davis, CA 95616, USA; Eng.) -Jannicke 01-158