Asymmetric catalysis in organic synthesis by Ryoji Noyori

By Ryoji Noyori

Offers with uncomplicated rules of uneven catalysis concentrating on its man made importance. Covers homogeneous uneven hydrogenation, uneven catalysis through chiral steel complexes, heterogeneous catalysis and non-organometallic catalysis. the gathering of a number stereoselective reactions illustrate a number of techniques and methodologies in addition to their normal application.

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156 O B B(Ipc)2 RO 14 R = Me 96 R = CH2OMe 97 R = CH2O(CH2)2TMS O O CO2Pr-i O O O B TBDMSO 98 O CO2Pr-i 99 CO2Pr-i O B B(Ipc)2 (i-Pr2N)Me2Si 100 B(Ipc)2 13 Me Me Si Ar O B 101 Ar = Ph 102 Ar = B(Ipc)2 Cl Ar N B(Ipc)2 Ar 103 104 Figure 7. Chiral 3-substituted allylic boron reagents. O CO2Pr-i O ALLYLBORATION OF CARBONYL COMPOUNDS 39 O B[(–)-Ipc]2 MOMO HO H (Eq. 69) Et2O, –78° OMOM (66%) 95% ee 96 To access anti-1,2-diols, indirect methods are required for the preparation of geometrically pure, chiral E-3-alkoxy reagents.

63,64,67,68,83,149 The enantiomerically pure α-substituted reagents of type 29/30 (Fig. 6, Eq. 39) react with benzaldehyde to give the expected homoallylic alcohol products such as 86 with high enantioselectivity (Eq. 85,86 By analogy with the abovedescribed reagents, the addition is presumed to occur through transition structure 85 with the pseudo-axial α-alkyl substituent. The competing transition structure with the pseudo-equatorial substituent would experience severe non-bonding interactions between this group and the bulky boronic ester moiety.

163 Aside from circumventing the need for a chiral boronate, these additions can lead to very good amplification of facial stereoselectivity. For example, compared to both non-catalyzed (room temperature, Eq. 90) and SnCl4 catalyzed variants, the use of the “matched” diol-SnCl4 enantiomer at a low temperature leads to a significant improvement in the proportion of the desired anti-syn diastereomer in the crotylation of aldehyde 117 with pinacolate reagent (Z)-7 (Eq. 93). Moreover, unlike reagent (Z)-11 (Eq.

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