- Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid
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Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.
- Torabi Kohlbouni, Saeedeh,Sarkar, Aritra,Zhang, Jun,Li, Xiaoyong,Borhan, Babak
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supporting information
p. 817 - 823
(2020/03/26)
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- Highly homogeneous stereocontrolled construction of quaternary hydroxyesters by addition of dimethylzinc to α-ketoesters promoted by chiral perhydrobenzoxazines and B(OEt)3
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A highly efficient enantioselective addition of Me2Zn to α-ketoesters, assisted by a chiral perhydro-1,3-benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α-hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α-ketoesters are employed. The catalyst can be recovered and reused without loss of activity.
- Infante, Rebeca,Nieto, Javier,Andres, Celia
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p. 4375 - 4379
(2012/05/20)
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- A concise synthesis of (S)-(+)-1-(4-{2-[bis-(4-fluorophenyl)methoxy]-ethyl} piperazin-1-yl)-2-phenylpropan-2-ol dimaleate
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(S)-(+)-1-(4-{2-[Bis-(4-fluorophenyl)methoxy]-ethyl}piperazin-1-yl) -2-phenylpropan-2-ol dimaleate was prepared in several steps from (S)-(+)-atrolactic acid by a process permitting synthesis of multigram quantities. With the information provided by asymmetric synthesis, the X-ray crystal structure was solved.
- Prisinzano, Thomas,Hsin, Ling-Wei,Folk, John E.,Flippen-Anderson, Judith L.,George, Clifford,Jacobson, Arthur E.,Rice, Kenner C.
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p. 3285 - 3289
(2007/10/03)
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