Room Temperature Asymmetric Allylic Trifluoromethylation of Morita–Baylis–Hillman Carbonates

(DHQD)2PHAL-catalyzed asymmetric allylic trifluoromethylation of Morita–Baylis–Hillman adducts using a Rupert–Prakash reagent is reported. This transformation provided the SN2′ trifluoromethylated products with good yields and excellent enantioselectivities at room temperature. It was also found tha...

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Published inOrganic letters Vol. 13; no. 22; pp. 6082 - 6085
Main Authors Li, Yun, Liang, Fang, Li, Qian, Xu, Yao-chang, Wang, Quan-Rui, Jiang, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2011
Amer Chemical Soc
Subjects
Carbonates - chemistry
Catalysis
Chemistry
Chemistry, Organic
Fluorine Compounds - chemistry
Methylation
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Temperature
NUCLEOPHILIC TRIFLUOROMETHYLATION
SUBSTITUTION
ALKYLATION
GAMMA-BUTENOLIDES
CONSTRUCTION
FLUORINE
ALDEHYDES
ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION
PHOSPHINE OXIDES
BASE
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Summary:(DHQD)2PHAL-catalyzed asymmetric allylic trifluoromethylation of Morita–Baylis–Hillman adducts using a Rupert–Prakash reagent is reported. This transformation provided the SN2′ trifluoromethylated products with good yields and excellent enantioselectivities at room temperature. It was also found that the reaction could be accelerated using acetonitrile as cosolvent.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202572u