4.2 Article

Synthesis of phospholane 1-oxide having oxygen functional groups from a 4-bromobutylphoshinate derivative

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HETEROCYCLES
卷 66, 期 -, 页码 251-261

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-05-S(K)15

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phospholane 1-oxide; phospha sugar; Grignard reaction; Michaelis-Arbuzov reaction; SDMA

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Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-0-methyl-L-threitol (12) in five steps. Reduction of 10a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane I-oxide (3), while the reaction of 10a with magnesium in boiling THF resulted in the formation of ethyl 2-methoxy-3-butenyl(phenyl)phosphinate (26).

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