Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8652-8653

  Yadav, Veejendra K ^a   Kumar, Naganaboina Vijaya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; MARINE TOXIN; METHANOL DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; PHASE TRANSITION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 3242676775     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048000c     Document Type: Article

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38. 2O led to elimination to form only one trisubstituted olefin shown below. This is possibly a consequence of exclusive 1,2-trans-elimination. (Diagram presented)
39. 2O (2 × 10 mL). The combined organic layer was dried, filtered, and concentrated. The crude material was purified by radial chromatography to obtain 3 (65 mg. 72%).
40. 2O (2 × 10 mL), and the combined organic extract was washed with water and brine, dried, filtered, and concentrated. The crude material was purified by radial chromatography for the products 4a/4b = 2:1, 67.3 mg, 78%; 10a/10b = 4:3, 54.3 mg, 65%.