By Hisashi Yamamoto, Kazuaki Ishihara
This two-volume set covers all new advancements and, furthermore, contains the new idea of mixed Bronsted and Lewis acid catalysis, built through Hisashi Yamamoto himself. the superb editorial crew has prepare an both best staff 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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Extra resources for Acid Catalysis in Modern Organic Synthesis, vol 1
22 Peng, F . G. (2007) journal of the American Chem ical Society, 1 29, 3070- 1 . 2 3 Xia, G . , Shibatomi, K . , Yamamoto, H. (2004) Synlett, 1 3 , 2437-9. 24 (a) Hanawa, H . , Maruoka, K. (2003) journal of the American Chemical Society, 125, 1 708-9. (b) Hanawa, H . , Uraguchi, D . , Konishi, S . , Maruoka, K. (2003) ChemistryA European journal, 9, 4405. , Maruoka, K. (2005) journal of the American Chemical Society, 1 27, 1 1 926-7. , Maruoka, K. (2006) journal of the American Chemical Society, 1 28, 2 1 74- 5 .
30) . The reactions proceed in useful yields and excellent enantioselectivities (84 to > 99% ee) . The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through hydrogen bonding. A similar mode of activation of the carbonyl group with TADDOL was indicated by the X-ray structure analysis of 1 : 1 complex of the related BAMO L derivative and benzaldehyde, suggesting the formation of B BA through intramolecular hydrogen bonding between the two hydroxyl groups and a single point activation of the carbonyl group through intermolecular hydrogen bonding.
C Ref. 10. d Ref. 1 1 . 27 -0. 1 Introd uction of Eiectron-Withdrawing G roup There are many factors which influence acidity. g. g. O H , N H , C H , etc . ) . Therefore, a simple strategy to develop more acidic Br0nsted acid would be to synthesize molecules which bear, along with the acidic site, several electron withdrawing groups andfor n-electron acceptors that form extensive conjugated systems with the anionic center of A- . According to Yagpolskii's principle, Koppel et al. reported that introduction of very strong electron-acceptor substituents such as =NTf and =N S 02 F into an acid 2 system instead of double bonded sp oxygen or sulfur atom increased the stability of counter anions and their acidity [4) .
Acid Catalysis in Modern Organic Synthesis, vol 1 by Hisashi Yamamoto, Kazuaki Ishihara