Highly Enantioselective 1,2-Addition of 2-[(Trimethylsilyl)oxy]furan to Aldehydes:  Application to Muricatacin Synthesis

TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1‘-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's b...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-07, Vol.63 (15), p.5169-5172
Main Authors: Szlosek, Magali, Franck, Xavier, Figadère, Bruno, Cavé, André
Format: Article
Language:English
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Summary:TMSOF 2-[(trimethylsilyl)oxy]furan has been used in an enantioselective aldol reaction for the first time. Indeed, addition of TMSOF to achiral aldehydes, in the presence (R)-1,1‘-bi-2-naphthol (Binol), gave the corresponding butenolides with moderate diastereomeric ratios (dr = 60%) and ee's between 60 and 90%. Application of this reaction to the total synthesis of annonaceous muricatacin in only two steps (in regards to the numerous multistep syntheses published so far) illustrated the efficiency of this strategy.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9804137