Acid Catalysis in Modern Organic Synthesis, vol 2 by Hisashi Yamamoto, Kazuaki Ishihara

By Hisashi Yamamoto, Kazuaki Ishihara

This two-volume set covers all new advancements and, moreover, comprises the recent suggestion of mixed Bronsted and Lewis acid catalysis, built through Hisashi Yamamoto himself. the superb editorial crew has prepare an both most sensible workforce of specialist authors, leading to a real treasure trove of crucial info -- making this a needs to for each chemist operating in natural chemistry and catalysis, in academia in addition to in undefined.

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It is known that diarylketones which are often resistant to other standard acetalization conditions [1 10]. It has been shown that a chemoselective deprotection of acetals in the presence of TH P and TB D M S ethers could be realized using Bi(OTf)3 •xH 2 0 as a catalyst. 1 1 . 2 Formation and Cleavage of Acylals Bi(N03 ) 3 • S H 2 0 [ 1 1 1a] and Bi(OTf) 3 •XH20 [ 1 1 1b] have been reported to be efficient catalysts (0. 1 mol%) for the formation of such protecting groups although BiCb has been used to catalyze their cleavage [ 1 1 2] .

Yadav, j . S . V. S . , Raghavender Rao, K. (2004) Tetrahedron Letters, 45, 6037-9. (a) De, S . K. A. (2005) Syn­ thesis, 8, 1 2 3 1 - 3 . M . , Samant, S . D . (2005) Tetrahedron Letters, 46, 6957-9. , Asim, M . C. (2004) Synlett, 1 5 , 2794-6. (b) Sreedhar, B . , Sridhar, C. (2004) Synthetic Communications, 34, 1433-40. , Gaspard­ Iloughmane, H . , Rogues, N . , L e Roux, C. (2003) Tetrahedron Letters, 44, 6379-82. Martin, R. (2000) Handbook of Hy­ droxybenzophenones, Kluwer Aca­ demic, Dordrecht.

The recent use of Bi(OTf) 3 ·xH20 in the synthesis of porphyrins has been reported although this catalyst gave a side product resulting from the scrambling of the porphyrins in contrast to some rare earth triftates ( 1 1 ] . Also reported is the synthesis of resorcinarenes (16b] and a patented process using Bi(OTf) 3 ·xH20 for the manufacture of tocopherol in which an alkylation reaction precedes a ring closure reaction (Equation 29) [57]. 0 OH + jBi(OTfb (0. 2 Acylation and Related Reactions Bismuth salts have been proved to be as active as RET or other metallic triflates in the FC acylation of aromatic compounds using acyl chlorides or anhydrides [50, 5 5 ] .

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