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Murai, K.; Fujioka, H., Science of Synthesis Knowledge Updates, (2016) 2, 313.
Optically active α-benzoyloxy- and α-hydroxyalkylphosphonates 37 and 38, respectively, are obtained by benzoylation of racemates in the presence of (4R,4′R)-2,2′-(propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole) [(R,R)-Ph-BOX, 36] (Scheme 25). The kinetic resolution gives good to excellent s values of up to 286. This reaction does not work for phenyl-substituted alcohols.[33]
Meeeee 88 Meeeeee Meeeeeeeee ee α-Meeeeee Meeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeee[88]
M8 | 88 | 88 | ee | Mee | ||
---|---|---|---|---|---|---|
ee (%) | Meeee (%) | ee (%) | Meeee (%) | |||
Me | 88 | 88 | 88 | 88 | 88 | [88] |
Me | >88 | 88 | 88 | 88 | 888 | [88] |
(M)-MM=MMMe | >88 | 88 | 88 | 88 | 888 | [88] |
Me | 88 | 88 | 88 | 88 | 88 | [88] |
(MM8)8MMMee | 88 | 88 | 88 | 88 | 88 | [88] |
e e = eeeeeeeeeee.
Meeeeee eeeeeeeeee ee eeeeeee α-eeeeeee eeeeeeeeeeee eee eeee eeee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee eeeee ee eeee/eeeeeeeee eeeeeeeeeee, eeeeeeeee eeeeee 88 eee eeeeeeeeeeeeeee eeeeeee eeeeeeeeeeee 88 (e eeeee = 88–888) (Meeeee 88). Me eeee eeeeeeee, eeeeeeeeeeeeee eeeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeeeeeee eeee eee eeeeeee eeeeeeeee ee eee eeeeeeee ee (M)-eeeeeeeeeeeeeeee [(M)-MMM, 88]. Meee eeeeeee ee eee eeeee eeeeeee ee eeeeeeeeeeeeeee eeeeeee eeeeeeeeee ee eeeeeee α-eeeeeee eeeeeeeeeeee, eee eeeeeeeee eeeeeeee eeee eeeeeeeeeee.[88]
Meeeee 88 Meeeeee Meeeeeeeee ee α-Meeeeee Meeeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeeee[88]
M8 | 88 | 88 | ee | Mee | ||
---|---|---|---|---|---|---|
ee (%) | Meeee (%) | ee (%) | Meeee (%) | |||
(MM8)8Me | 88 | 88 | >88 | 88 | 888 | [88] |
Me | 88 | 88 | 88 | 88 | 888 | [88] |
Me | 88 | 88 | >88 | 88 | 888 | [88] |
MM8MMMMMM | 88 | 88 | 88 | 88 | 888 | [88] |
(MM8)8MMMee | 88 | 88 | >88 | 88 | 88 | [88] |
e e = eeeeeeeeeee.
References
[33] | Meeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[34] | Meeeee, M.; Mee, M.; Meeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888) 88, 88 888. |