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3. Selected, recent work in this field: (a) M. Mohebbi, M. Bararjaian, S. N.
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16. Prolinamine 8e, which possesses a secondary pyrrolidine nitrogen atom,
might also adopt transition states of type 15 (with NHMe instead of
NMe2).
17. The low enantioselectivities obtained with the linear aliphatic and vinylic
aldehydes 1c and 1l (17% and 62% ee, respectively, see Table 4) are
most likely not caused by a diminished preference of 13A over 13B–D,
but the consequence of an interfering coordination mode of these
aldehydes via their cis lone pair, which gives the enantiomeric product.
18. We assume that the pseudo-equatorial orientation of the 5-cis substituent
locks the pictured envelope conformation of the central diazazincolidine
in 13A–D, thus creating the rigid backbone required for high asymmetric
inductions (see Figure 1 and discussion). It might be possible that larger
substituents R1 and R3, which would have to occupy pseudo-equatorial
positions in the 'locked conformation' of 13, destabilize that
conformation, resulting in a conformationally flexible backbone and
different transition states with low stereocontrol.
19. A comparable drastic loss in enantioselectivity was also observed in Cu-
catalyzed oxidative biaryl couplings.8c
20. Coordination of Et2Zn to a sulfonamide group was proposed to occur via
the nitrogen atom13a and via an oxygen atom.13d
21. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals,
Butterworth-Heinemann: Oxford, 2000.
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Scharnagel, D.; Breuning, M. Synthesis 2015, 47, 575–586.
10. Synthesis of 5-cis-substituted α,α-diphenylprolinols: (a) Trost, B. M.;
Miege, F. J. Am. Chem. Soc. 2014, 136, 3016–3019; (b) Nyerges, M.;
Bendell, D.; Arany, A.; Hibbs, D. E.; Coles, S. J.; Hursthouse, M. B.;
Groundwater, P. W.; Meth-Cohn, O. Tetrahedron 2005, 61, 3745−3753;
(c) Ref. 12.
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