A versatile stereocontrolled approach to chiral tetrahydrofuran and tetrahydropyran derivatives via sequential asymmetric horner-wadsworth-emmons and palladium-catalyzed ring closure reactions

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2611-2614

  Vares, Lauri ^a,b,c,d   Rein, Tobias ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^c TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^d NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001574002     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006135r     Document Type: Article

References (37)

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32. See Supporting Information for details on how compound 8 was prepared.
33. 1H NMR spectroscopy. The absolute configurations of compounds 12 and 16 were assigned on the basis of NMR analyses of the corresponding Mosher esters (see Supporting Information for details).
34. From the reaction between 8 and 9a, bisaddition products were also isolated in ca. 40% yield, which explains the modest yield of compound 10.
35. Depending on the specific conditions used, varying ratios between the secondary alcohols (12, 16, 20, and 23) and the isomeric primary alcohols (11, 15, 19, and 22, respectively) could be obtained from reduction of the corresponding HWE products. The primary alcohols could be separated and converted to mixtures of secondary/primary, thereby increasing the overall yield of the desired secondary alcohols to ca. 70% after one iteration (see Supporting Information for details).
36. Neocuproine = 2,9-dimethyl-1.10-phenanthroline.
37. 13C NMR analysis of a derivative (see Supporting Information for details).