A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol

Hong Kui Zhang; Wing Hong CHAN; Albert W M LEE; Ping Fang Xia; Wai Yeung WONG

doi:10.1016/j.cclet.2007.04.001

A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol

Hong Kui Zhang^*
, Wing Hong CHAN
, Albert W M LEE
, Ping Fang Xia
, Wai Yeung WONG

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

4 Citations (Scopus)

Abstract

Reductive cleavage of the N{single bond}O bond of isoxazolidine ring with catalytic hydrogenation over Raney nickel was described. Bicyclic isoxazolidines could be effectively converted into the corresponding 1,3-amino-alcohol possessing a sultone or sultam moiety with high conversion and yield when the hydrogenation was catalyzed by freshly prepared Raney nickel under a pressure of 40 psi in the presence of triethylamine.

Original language	English
Pages (from-to)	629-632
Number of pages	4
Journal	Chinese Chemical Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.cclet.2007.04.001
Publication status	Published - Jun 2007

User-Defined Keywords

1,3-Amino-alcohol
Hydrogenation
Isoxazolidine
Raney nickel

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10.1016/j.cclet.2007.04.001

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@article{dea27ba0179e4e27bc66a1c0858c5c62,

title = "A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol",

abstract = "Reductive cleavage of the N\{single bond\}O bond of isoxazolidine ring with catalytic hydrogenation over Raney nickel was described. Bicyclic isoxazolidines could be effectively converted into the corresponding 1,3-amino-alcohol possessing a sultone or sultam moiety with high conversion and yield when the hydrogenation was catalyzed by freshly prepared Raney nickel under a pressure of 40 psi in the presence of triethylamine.",

keywords = "1,3-Amino-alcohol, Hydrogenation, Isoxazolidine, Raney nickel",

author = "Zhang, \{Hong Kui\} and CHAN, \{Wing Hong\} and LEE, \{Albert W M\} and Xia, \{Ping Fang\} and WONG, \{Wai Yeung\}",

year = "2007",

month = jun,

doi = "10.1016/j.cclet.2007.04.001",

language = "English",

volume = "18",

pages = "629--632",

journal = "Chinese Chemical Letters",

issn = "1001-8417",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol

AU - Zhang, Hong Kui

AU - CHAN, Wing Hong

AU - LEE, Albert W M

AU - Xia, Ping Fang

AU - WONG, Wai Yeung

PY - 2007/6

Y1 - 2007/6

N2 - Reductive cleavage of the N{single bond}O bond of isoxazolidine ring with catalytic hydrogenation over Raney nickel was described. Bicyclic isoxazolidines could be effectively converted into the corresponding 1,3-amino-alcohol possessing a sultone or sultam moiety with high conversion and yield when the hydrogenation was catalyzed by freshly prepared Raney nickel under a pressure of 40 psi in the presence of triethylamine.

AB - Reductive cleavage of the N{single bond}O bond of isoxazolidine ring with catalytic hydrogenation over Raney nickel was described. Bicyclic isoxazolidines could be effectively converted into the corresponding 1,3-amino-alcohol possessing a sultone or sultam moiety with high conversion and yield when the hydrogenation was catalyzed by freshly prepared Raney nickel under a pressure of 40 psi in the presence of triethylamine.

KW - 1,3-Amino-alcohol

KW - Hydrogenation

KW - Isoxazolidine

KW - Raney nickel

UR - https://www.scopus.com/pages/publications/34249776043

U2 - 10.1016/j.cclet.2007.04.001

DO - 10.1016/j.cclet.2007.04.001

M3 - Journal article

AN - SCOPUS:34249776043

SN - 1001-8417

VL - 18

SP - 629

EP - 632

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 6

ER -

A novel reductive ring-opening reaction of isoxazolidine to form functionalized 1,3-amino-alcohol

Abstract

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