Memory of chirality in the transannular cyclization of cyclodecenyl radicals.
The transannular cyclization of an enantioenriched cyclodecenyl radical proceeds in a 5-exo fashion to produce scalemic bicyclo[5.3.0]decanes. This cyclization is notable because it demonstrates chirality transfer through conformational memory of an unstabilized secondary radical. [reaction: see text]
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, CA 92697, USA.
Jackline E
JE
Dalgard
Scott D
SD
Rychnovsky
D000473:Alkanes / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000473:Alkanes; D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D005609:Free Radicals; C012867:decane