An inexpensive and simple process for the preparation of antimony(III) and bismuth(III) triflates

Peyronneau, Magali; Arrondo, C.; Vendier, Laure; Roques, Nicolas; Roux, Christophe Le

doi:10.1016/j.molcata.2003.10.020

Cited by 34 publications

(2 citation statements)

References 20 publications

(34 reference statements)

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“…Bismuth salts have been reported as catalysts for opening of epoxides, Mannich-type reactions, formation and deprotection of acetals, Friedel−Crafts reactions, Fries and Claisen rearrangements, and Sakurai reactions . Bi(OTf) 3 is particularly attractive because it is commercially available or can be easily prepared from commercially available starting materials …”

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confidence: 99%

Diastereoselective Mukaiyama Aldol Reaction of 2-(Trimethylsilyloxy)furan Catalyzed by Bismuth Triflate

2007

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We have developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in low catalyst loading (1 mol %). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl)furan-2(5H)-ones in high yields with good to very good diastereoselectivities (dr up to >98:2). Such selectivities, albeit previously reported with other Lewis acids, could this time be achieved with a much lower catalyst loading. 5-(Hydroxy(alkyl)methyl)furan-2(5H)-ones derived from ketones could also be obtained with good diastereoselectivities.

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confidence: 99%

Diastereoselective Mukaiyama Aldol Reaction of 2-(Trimethylsilyloxy)furan Catalyzed by Bismuth Triflate

2007

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“…Bismuth salts have been reported as catalysts for opening of epoxides, Mukaiyama-aldol reactions, formation and deprotection of acetals, Friedel−Crafts reactions, Diels−Alder reactions, and intramolecular Sakurai cyclizations . Bi(OTf) 3 is particularly attractive because it is commercially available or can be easily prepared from commercially available starting materials …”

mentioning

confidence: 99%