Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity
Publication type: Journal Article
Publication date: 1992-10-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetale (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 reduced 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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Nanjappan P., Ramalingam K., Nowotnik D. J. Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity // Tetrahedron Asymmetry. 1992. Vol. 3. No. 10. pp. 1271-1282.
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Nanjappan P., Ramalingam K., Nowotnik D. J. Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity // Tetrahedron Asymmetry. 1992. Vol. 3. No. 10. pp. 1271-1282.
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TY - JOUR
DO - 10.1016/s0957-4166(00)82085-6
UR - https://doi.org/10.1016/s0957-4166(00)82085-6
TI - Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity
T2 - Tetrahedron Asymmetry
AU - Nanjappan, P
AU - Ramalingam, K
AU - Nowotnik, D J
PY - 1992
DA - 1992/10/01
PB - Elsevier
SP - 1271-1282
IS - 10
VL - 3
SN - 0957-4166
SN - 1362-511X
ER -
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@article{1992_Nanjappan,
author = {P Nanjappan and K Ramalingam and D J Nowotnik},
title = {Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity},
journal = {Tetrahedron Asymmetry},
year = {1992},
volume = {3},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/s0957-4166(00)82085-6},
number = {10},
pages = {1271--1282},
doi = {10.1016/s0957-4166(00)82085-6}
}
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Nanjappan, P., et al. “Synthesis of the four stereoisomers of 1-azabicyclo[2.2.2]oct-3-yl-α-hydroxy-α-(4-phenylboronic acid)-α-phenylacetate (QNB-boronic acid), including a preparative HPLC method to separate diastereoisomeric mixtures with high optical purity.” Tetrahedron Asymmetry, vol. 3, no. 10, Oct. 1992, pp. 1271-1282. https://doi.org/10.1016/s0957-4166(00)82085-6.