Chirality multiplication and efficient chirality transfer in exo- and endo-radical cyclization reactions of 4-(4 '-iodobutyl)quinolones

[GRAPHICS] Enantioselective radical cyclization reactions were performed in the presence of chiral complexing agent 1. The title compounds 3 yielded, depending on the 3'-substitution (R = H, Me), the corresponding endo- (4) or exo-product (5). The highest enantioselectivities (99% and 94% ee) w...

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Published inOrganic letters Vol. 8; no. 14; pp. 3145 - 3147
Main Authors Dressel, Martina, Bach, Thorsten
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.07.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HOST
MODEL
STEREOSELECTIVITY
REGIOSELECTIVITY
ALLYLATION
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Summary:[GRAPHICS] Enantioselective radical cyclization reactions were performed in the presence of chiral complexing agent 1. The title compounds 3 yielded, depending on the 3'-substitution (R = H, Me), the corresponding endo- (4) or exo-product (5). The highest enantioselectivities (99% and 94% ee) were achieved with 2.5 equiv of complexing agent. The cyclization product trans-4 was obtained in 55% ee in the presence of only 0.1 equiv of complexing agent.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol061194b