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


By Hisashi Yamamoto, Kazuaki Ishihara

ISBN-10: 3527317244

ISBN-13: 9783527317240

This two-volume set covers all new advancements and, additionally, contains the recent inspiration of mixed Bronsted and Lewis acid catalysis, constructed by means of Hisashi Yamamoto himself. the superb editorial group has prepare an both most sensible crew 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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1999) journal of the Chem­ ical Society. Perkin Transactions 1, 8, 873-8. (b) Peterson, K. E . , Smith, R . C . S. (2003) Tetrahedron Letters, 44, 772 3 - 5 . (a) Labrouillere, M . , L e Roux, C . , Oussaid, A . , Gaspard-Iloughmane, H . , Dubac, J. (1995) Bulletin de la Societe Chimique de France, 132, 522- 30. , Gaspard-IIoughmane, H . , Dubac, J. (1 994) Synlett, 9, 723 -4. , Gaspard­ Iloughmane, H . , Dubac, J. (1994) journal of Organic Chemistry, 59, 2238-40. , Sandhu, S . S . (1959) journal of the Chemical Society, 319-22.

3 Protection of the Thiol G roup BiOCl04•xH2 0 [103] and BiCb [104] have been reported as catalysts for the acetylation of aliphatic and aromatic thiols. 1 1 . 4 Protection of the Amino G roup Cyclic N ,O-aminals can be chemoselectively cleaved in the presence of O,O-acetals using a catalytic amount of BiBr3 in acetonitrile (Equation 46) [1 14]. Other amine protective groups as well as MOM, Cbz, Ac, protecting groups for hydroxyl functions are stable under these conditions. It is noteworthy that the reaction rates could be accelerated by adding a catalytic amount of water revealing again the B LA behavior of such bismuth catalysis.

Moreover, neither racemization nor epimerization of the substrates were detected during the acylation process with Bi(OTf) J •XHzO. The activity of Bi(OTf) J •4HzO has been extended to a large scale acylation of alcohols, 1 , 2 and 1 , 3-diols process [lOb] . Mention has to be made about the interesting reaction called by the authors a shotgun process [1 02c] , a process where the regioselective acylation ofhomoallylic alcohols is involved. Inter­ estingly, BiOCl has been reported as an efficient procatalyst for the in situ formation of BiCb from the reaction between BiOCl and acetyl chloride [ 1 04] .

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