Gawley Robert E, Narayan Sanjay, Vicic David A
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
J Org Chem. 2005 Jan 7;70(1):328-9. doi: 10.1021/jo048569w.
Enantiopure 2-(tributylstannyl)pyrrolidine hydroiodide may be prepared in excellent yield by TMSI treatment of the corresponding N-Boc compound, which is in turn prepared by asymmetric deprotonation (s-BuLi.sparteine) and stannylation, as described in the literature. Crystals of the hydroiodide salt suitable for X-ray analysis were obtained, and although there is some disorder about the butyl groups, analysis using anomalous dispersion establishes the absolute configuration as S.
