Regio- and Diastereoselective Crotylboration of vic-Tricarbonyl Compounds

Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid prom...

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Veröffentlicht in:European journal of organic chemistry 2013-02, Vol.2013 (4), p.662-665
Hauptverfasser: Roßbach, Jan, Baumeister, Julia, Harms, Klaus, Koert, Ulrich
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Sprache:eng
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Zusammenfassung:Crotylboration of vic‐diketoamides and vic‐diketo esters was achieved with high diastereoselectivity and complementary regioselectivity. Whereas (E)‐crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti), Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer. (E)‐Crotylboration of α,β‐diketoamides resulted in high yields (91–99 %) of β‐crotylated products obtained as a single diastereomer (anti). Lewis acid promoted crotylboration of α,β‐diketo esters yielded the α‐crotylated species with the anti product as main diastereomer.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201517