Catalytic asymmetric synthesis of quaternary α-hydroxy trifluoromethyl phosphonate via chiral aluminum(III) catalyzed hydrophosphonylation of trifluoromethyl ketones

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4296-4299

  Zhou, Xin ^a   Zhang, Qi ^a   Hui, Yonghai ^a   Chen, Weiliang ^a   Jiang, Jun ^a   Lin, Lili ^a   Liu, Xiaohua ^a   Feng, Xiaoming ^a,b  

^a Sichuan University   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXY TRIFLUOROMETHYL PHOSPHONATE; ALPHA-HYDROXY TRIFLUOROMETHYL PHOSPHONATE; ALUMINUM; FLUORINE DERIVATIVE; KETONE; LIGAND; ORGANOPHOSPHORUS COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; METHYLATION; PHOSPHORYLATION; STEREOISOMERISM; SYNTHESIS;

ALUMINUM; CATALYSIS; FLUORINE COMPOUNDS; HYDROXYLATION; KETONES; LIGANDS; METHYLATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHORYLATION; STEREOISOMERISM;

EID: 77957174098     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101737b     Document Type: Article

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49. 4 catalyzed the hydrophosphonylation of trifluoromethyl ketone smoothly, giving the corresponding quaternary α-hydroxy trifluoromethyl phosphonates with 70% yield. However, the phospha-Brook rearrangement also occurred, and 23% yield of α- trifluoromethyl phosphate was obtained.
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58. The relationship between the enantiomeric excess of the chiral ligand L5 and the product 8a was investigated. Linear effect was observed, which implied that the reaction was performed in the presence of monomeric aluminum species.