Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines
by Gawley, R. E.; Eddings, D. B.; Santiago, M.; Vicic, D. A.
N-Methyl trans-fused perhydroisoindolines substituted with a tributylstannyl group in the 2-position have been prepared and used as precursors of the corresponding alpha-aminoorganolithiums. The steric course of the reactions of these and other conformationally rigid organolithiums with various electrophiles is summarized and compared with the steric course of the unsubstituted analogs. A mechanistic rationale for the steric course of electrophilic substitutions of these organolithiums is discussed. Pathways involving both polar electrophilic substitutions and radical couplings were observed with different electrophiles.
- Journal
- Organic and Biomolecular Chemistry
- Volume
- 4
- Issue
- 23
- Year
- 2006
- Start Page
- 4285-4291
- URL
- https://dx.doi.org/10.1039/b608013h
- ISBN/ISSN
- 1477-0539; 1477-0520
- DOI
- 10.1039/b608013h