Allylation and Crotylation of Ketones and Aldehydes Using Potassium Organotrifluoroborate Salts under Lewis Acid and Montmorillonite K10 Catalyzed Conditions

Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF3·OEt2 and montmorillonite clay are used as catalysts to promote additions. The montmorilloni...

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Bibliographic Details
Published inOrganic letters Vol. 11; no. 12; pp. 2631 - 2634
Main Authors Nowrouzi, Farhad, Thadani, Avinash N, Batey, Robert A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC ALLYLBORATION
ACTIVATION
ANTI CROTYLATION
REAGENTS
SCOPE
PERSPECTIVES
ENANTIOSELECTIVE ALLYLBORATION
CARBONYL-COMPOUNDS
HIGHLY DIASTEREOSELECTIVE SYN
TRIFLUOROBORATE
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Summary:Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF3·OEt2 and montmorillonite clay are used as catalysts to promote additions. The montmorillonite-catalyzed method in particular is very robust, providing a straightforward and scalable method for the allylation and crotylation of a range of ketones and aldehydes.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol900599q