Catalytic asymmetric conjugate addition of α-cyanoketones for the construction of a quaternary stereogenic center

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1484-1487

  Kawato, Yuji ^a   Takahashi, Noriko ^a   Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77950233676     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100183s     Document Type: Article

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60. 3/1 ) 1:1 gave the product in 91% yield and 24% ee under otherwise identical conditions.
61. The absolute configuration of 4aa and 4ac was determined by X-ray crystallographic analysis. See Supporting Information for details.
62. The reaction using an acyclic α-cyanoketone or a β-substituted enone gave no desired products. Experimental details are summarized in Supporting Information.
63. The reaction with enone 3n using another RE/1 catalyst did not improve the enantioselectivity. The results are summarized in Supporting Information.
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69. Relative configuration was determined after converting to the corresponding cyclic carbonate. See Supporting Information for details.