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

Tadashi Hanaya; Shigeru Kawase; Hiroshi Yamamoto

doi:10.3987/COM-05-S(K)15

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

Tadashi Hanaya, Shigeru Kawase, Hiroshi Yamamoto

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6 Citations (Scopus)

Abstract

Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-O-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 1-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).

Original language	English
Pages (from-to)	251-261
Number of pages	11
Journal	Heterocycles
Volume	66
Issue number	1
DOIs	https://doi.org/10.3987/COM-05-S(K)15
Publication status	Published - Dec 31 2005

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Synthesis of phospholane 1-oxide having oxygen functional groups from a 4-bromobutylphoshinate derivative",

abstract = "Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-O-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 1-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).",

author = "Tadashi Hanaya and Shigeru Kawase and Hiroshi Yamamoto",

year = "2005",

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doi = "10.3987/COM-05-S(K)15",

language = "English",

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T1 - Synthesis of phospholane 1-oxide having oxygen functional groups from a 4-bromobutylphoshinate derivative

AU - Hanaya, Tadashi

AU - Kawase, Shigeru

AU - Yamamoto, Hiroshi

PY - 2005/12/31

Y1 - 2005/12/31

N2 - Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-O-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 1-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).

AB - Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-O-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 1-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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JO - Heterocycles

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ER -

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

Abstract

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