By Hisashi Yamamoto, Kazuaki Ishihara

ISBN-10: 3527317244

ISBN-13: 9783527317240

This two-volume set covers all new advancements and, furthermore, comprises the new inspiration of mixed Bronsted and Lewis acid catalysis, constructed by means of Hisashi Yamamoto himself. the superb editorial group has prepare an both best staff of specialist authors, leading to a real treasure trove of crucial details -- 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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Extra info for Acid Catalysis in Modern Organic Synthesis, vol 1

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Various tricyclic skeletons have been synthesized with good enantioselectivities (79-85% ee) in the presence of chiral LBA (1 5 ) . -9 Br r:{ 6H � o � � ;; .... 23 S nCI4-ch i ral pyrogal l o l com p l ex (1 5) as a new LBA fo r ena ntioselective polyene cyclizatio n . Chiral catechol-derived L B A ( 1 6 ) was devised as a new artificial cyclase for polyprenoids by the same group in 2004 (Scheme 1 . 24) [27]. The synthetic power of the new chiral LBA (16) has been well demonstrated by enantios­ elective cyclizations of various 2-(polyprenyl)phenol derivatives with good to excellent enantioselectivities (88- 90% ee) , leading to the efficient asymmetric syn­ theses of ( - )-chromazonarol, (+) -8-epi-puupehedione, and ( - ) - 1 1 '-deoxytaondiol methyl ether.

2005) Angewandte Chemie Inter­ national Edition, 44, 1484-7. , Helal, CJ . (1998) Angewandte Chemie Interna­ tional Edition, 110, 2092 - 1 18. , Yamamoto, H. (eds) (1999) Comprehensive Asymmetric Catalysis, Springer, Germany, Vol. I , p. 290. 20 Jacobsen, E . N . , Yamamoto, H. (eds) (2004) Comprehensive 34 1 Recent Advance of'Combined Acid' Strategy for Asymmetric Catalysis 1 Asymmetric Catalysis, Springer, Germany, Sup!. 2, p. 7. 21 Liu, D . , Corey, E . J . (2007) journal of the American Chemical Society, 1 29, 1498-9.

The authors proposed that the B B A form o f (27) i s responsible for the active catalyst in this system and the reaction proceeds in a stepwise fashion initiated with N-nitroso aldol reaction, followed by Michael addition of the resulting anionic oxygen atom. Schaus and coworkers have developed a general route to the Clerodane diter­ pene core by the use of previously developed Bmnsted acid catalyzed asymmetric Morita- Baylis- Hillman ( M B H ) reactionf Lewis acid mediated ring-annulation pro­ cess (Scheme 1 .

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Acid Catalysis in Modern Organic Synthesis, vol 1 by Hisashi Yamamoto, Kazuaki Ishihara


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