Absolute configuration of 2-(tributylstannyl)pyrrolidine by anomalous dispersion X-ray analysis

by Gawley, Robert E.; Narayan, Sanjay; Vicic, David A.

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.

Journal
Journal of Organic Chemistry
Volume
70
Issue
1
Year
2005
Start Page
328
ISBN/ISSN
0022-3263; 1520-6904
DOI
10.1021/jo048569w