Highly enantioselective organocatalytic Michael addition reactions of ketones with chalcones

Advanced Synthesis and Catalysis

Volumn 348, Issue 4-5, 2006, Pages 425-428

  Wang, Jian ^a   Li, Hao ^a   Zu, Liansuo ^a   Wang, Wei ^a,b  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric catalysis; Enones; Ketones; Michael addition; Organic catalysis; Pyrrolidine sulfonamides

Indexed keywords

EID: 33645929387     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200505420     Document Type: Article

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53. 2O, no reactions were observed.
54. Acyclic ketones were also evaluated including acetone, 3-pentanone, and acetophenone, unfortunately no reaction occurred. Isovaleraldehyde (1 equiv.) was also tested in an initial study with 4′-chlorochalcone (3 equivs.) and afforded an adduct in 22% yield, 50:1 dr, 52% ee using 20 mol % II in DMSO/i-PrOH (1/1) at room temperature for 4 d.
55. No reaction was observed for benzylideneacetone probably due to its less reactivity than chalcones.
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