Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 4, Pages 662-665Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201517
Keywords
Synthetic methods; vic-Tricarbonyl compounds; Crotylboration; Regioselectivity; Diastereoselectivity
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Funding
- Deutsche Forschungsgemeinschaft (DFG)
- Fonds der Chemischen Industrie
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Crotylboration of vic-diketoamides and vic-diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)-crotylboration of alpha,beta-diketoamides resulted in high yields (91-99%) of beta-crotylated products obtained as a single diastereomer (anti), Lewis acid promoted kcrotylboration of alpha,beta-diketo esters yielded the alpha-crotylated species with the anti product as main diastereomer.
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