Rapid, parallel synthesis of homoallylic alcohols by lewis acid mediated allylations of aldehydes with new fluorous allyl stannanes

Medicinal Chemistry Research

Volumn 8, Issue 4-5, 1998, Pages 261-265

  Curran, Dennis P ^a   Luo, Zhiyong ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKANE; ALLYL ALCOHOL; FLUORINE DERIVATIVE; ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL REACTION; FILTRATION; METHODOLOGY; SYNTHESIS;

EID: 0031740765     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

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22. 2, 0.33 ml, 0.33 mmol) was added to a solution of 2-nitrobenzaldehyde (45 mg, 0.30 mmol) in dry THF at -78°C. To the resulting white suspension, a solution of 2b (408 mg, 0.33 mmol) in dry THF was added slowly at -78°C. The mixture was stirred at -78°C for 1.5 h, and warmed to room temperature over 5 h before quenching with few drops of dilute NaOH. After concentration, the mixture was loaded onto a short column with 3.5 g fluorous RP silica gel and eluted with 8 ml acetonitrile to give pure product. In the parallel synthesis, the eight reaction mixtures were purified simultaneously with SPE-24G vacuum manifold. All products were compared with authentic samples as in reference 3i.