Inverse temperature dependence in the diastereoselective addition of grignard reagents to a tetrahydrofurfural

Organic Letters

Volumn 11, Issue 10, 2009, Pages 2057-2060

  Mowat, Jeffrey ^a   Kang, Baldip ^a   Fonovic, Branden ^b   Dudding, Travis ^b   Britton, Robert ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

^b BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYTETRAHYDROFURFURAL; 3-HYDROXYTETRAHYDROFURFURAL; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FURFURAL;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; TEMPERATURE;

CATALYSIS; FURALDEHYDE; INDICATORS AND REAGENTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM; TEMPERATURE;

EID: 66149114385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900324s     Document Type: Article

References (62)

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60. 2Mg (1 M solution in heptane) to a solution of 1 in DCE at room temperature provided (in low yield) a 1.3:1 mixture of diastereomeric alcohols favoring the 10S diastereomer, along with a number of byproducts.
61. 2O (1.8:1). In DCE, the ratio of 10R:10S diastereomers (2.3:1) was unchanged when the addition was carried out at temperatures ranging from room temperature to 83 °C.
62. See Supporting Information for theoretical references as well as a comprehensive explanation of methods used to locate the transition states.