Asymmetric [4+2] cycloadditions employing 1,3-dienes derived from (R)-4-t-butyldimethyl-silyloxy-2-cyclohexen-1-one

Tetrahedron Letters

Volumn 50, Issue 48, 2009, Pages 6621-6623

  Hua, Zhengmao ^a   Chen, Lei ^a   Mei, Yan ^a   Jin, Zhendong ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIENE DERIVATIVE; 4 TERT BUTYLDIMETHYLSILYLOXY 2 CYCLOHEXEN 1 ONE; ALKADIENE; KETONE DERIVATIVE; MALEIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; ISOMERISM; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 70349770679     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.055     Document Type: Article

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33. 2 in the presence of pyridine to provide (R)-4-(t-butyldimethylsilyloxy)-2-iodo-2-cyclohexen-1-one in 63% yield, which was transformed to 24 in 71% yield via the same procedure used in the preparation of 9.
34. Synthesis of compound 26: compound 1 reacted with LDA followed by the addition of MeI to give (4R)-4-(t-butyldimethylsilyloxy)-6-methyl-2-cyclohexen-1-one in 66% yield, which was transformed to 26 in 92% yield via the same procedure used in the preparation of 9.
35. Synthesis of compound 28: conjugate addition of lithium cyano methyl cuprate to compound 1 in the presence of TMSCl provided silyl enol ether that underwent Saegusa oxidation to give (4R)-3-methyl-4-(t-butyldimethylsilyloxy)-2-cyclohexen-1-one in 68% yield, which was transformed to 28 in 84% yield via the same procedure used in the preparation of 9.
36. Synthesis of compound 30: conjugate addition of lithium cyano n-butyl cuprate to compound 1 in the presence of TMSCl provided silyl enol ether that underwent Saegusa oxidation to give (4R)-3-n-butyl-4-(t-butyldimethyl-silyloxy)-2-cyclohexen-1-one in 70% yield. Treatment with LDA followed by the addition of MeI afforded (4R)-3-n-butyl-4-(t-butyldimethylsilyloxy)-6-methyl-2-cyclohexen-1-one in 82% yield, which was transformed to 30 in 70% yield via the same procedure used in the preparation of 9.