Tetrahedron Asymmetry p. 1271 - 1282 (1992)
Update date:2022-08-04
Topics:
Nanjappan, P.
Ramalingam, K.
Nowotnik, D. P.
The four stereoisomers of 1-azabicyclo<2.2.2>oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB boronic acids, 1a-1d) were synthesized initially via 1-azabicyclo<2.2.2>oct-3-yl-α-hydroxy-α-(4-iodophenyl)-α-phenylacetate (iodo-QNBs, 6a-6d) using an adaptation of a published procedure.The number of steps involved were reducted substantially using a distinctly different approach.This involved the synthesis of diastereoisomers of QNB-boronic acid, followed by separation and isolation of enantiomers by preparative reversed-phase HPLC.An improved method of synthesis of α-hydroxy-α-(4-aminophenyl)-α-phenyl-acetic acid (3a and 3b) from α-hydroxy-α-(4-nitrophenyl)-α-phenylacetic acid (2a and 2b) is also described.
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Doi:10.1007/s10593-018-2237-7
()Doi:10.1002/chem.201203462
(2013)Doi:10.1007/s00044-013-0726-x
(2014)Doi:10.1039/c39920001571
(1992)Doi:10.1016/j.tetasy.2013.05.028
(2013)Doi:10.1016/j.tet.2021.131927
(2021)