Tetrahedron Asymmetry p. 2183 - 2198 (1993)
Update date:2022-09-26
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Kiesewetter
Our program on the synthesis of 18F-labeled muscarinic receptor ligands required the preparation of chiral fluoroalkyl benzilic acids. An enantioselective synthesis of substituted benzilic acids was achieved using 8-phenylmenthol as the chiral auxiliary. Grignard addition to the si face of 8-phenylmenthyl benzoylformate 7 proceeded with high selectivity. The results of the chiral induction support assignments of the chirality of benzilic acids previously resolved by crystallization. The method was used to synthesize (R)-quinuclidinyl-(R)-4-iodo)benzilate, which proved identical to an authentic sample. In addition, the method allows the preparation of (R)- and (S)-fluoroethyl benzilic acids in a stereoselective manner.
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Doi:10.1055/s-1993-25947
(1993)Doi:10.1021/ol401801g
(2013)Doi:10.1002/chem.201301398
(2013)Doi:10.1021/jo401283x
(2013)Doi:10.1016/S0040-4020(01)88311-3
(1992)Doi:10.1021/jm00041a003
(1994)