Stereochemistry of the addition of dialkyl phosphites to (S)-N,N-dibenzylphenylglycinal |
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| Affiliation: | 1. Department of Civil and Environmental Engineering, University of Massachusetts Lowell, Lowell, MA, United States;2. Department of Electrical and Computer Engineering, University of Massachusetts Lowell, Lowell, MA, United States;1. Centre for Bioinnovation, University of the Sunshine Coast, Sippy Downs, QLD 4556, Australia;2. School of Science and Engineering, University of the Sunshine Coast, Sippy Downs, QLD 4556, Australia;3. Mosquito Control Laboratory, QIMR Berghofer Medical Research Institute, 300 Herston Road, Herston, QLD 4006, Australia;1. Department of Software Convergence, Sejong University, 209 Neungdong-ro, Gwangjin-gu, Seoul, South Korea;2. Department of Electronics and Information Engineering, Sejong University, 209 Neungdong-ro, Gwangjin-gu, Seoul, South Korea;3. Department of Intelligent and Mechatronics Engineering, Sejong University, 209 Neungdong-ro, Gwangjin-gu, Seoul, South Korea;4. Department of Semiconductor System Engineering, Sejong University, 209 Neungdong-ro, Gwangjin-gu, Seoul, South Korea;1. Institute for Bioengineering of Catalonia (IBEC), The Barcelona Institute of Science and Technology, Baldiri Reixac 10-12, 08028 Barcelona, Spain;2. Department of Electronics and Biomedical Engineering, University of Barcelona, Marti i Franqués 1, 08028 Barcelona, Spain;1. College of Electronic and Information Engineering, Southwest University, Chongqing 400715, China;2. Department of Electronics, Graduate School of Information Science and Electrical Engineering, Kyushu University, Fukuoka 819-0395, Japan |
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| Abstract: | The addition of various dialkyl phosphite derivatives to (S)-N,N-dibenzylphenylglycinal 6 led to the preponderance of anti over syn diastereoisomers: from 75:25 when NEt3 or Ti(OiPr)4 were used to 51:49 for Li or Mg salts. In the NEt3-catalysed reaction, partially racemised phosphonates were formed, while enantiomeric products were obtained after addition of lithium O,O-dimethylphosphonate to (S)-6 at −70°C. Because the syn-isomers were found to be resistant to O-benzoylation, mixtures of diastereoisomers were easily separated after esterification of the anti products. Hydrogenation of the syn-phosphonates in the presence of Boc2O gave enantiomeric dialkyl N-Boc-2-amino-1-hydroxy-2-phenylethylphosphonates—phosphonate analogues of the docetaxel C-13 side chain. |
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