Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones

Dharmendra Kumar Tiwari; Ashif Y. Shaikh; Laxmikant S. Pavase; Vikas K. Gumaste; Abdul Rakeeb A S Deshmukh

doi:10.1016/j.tet.2006.12.010

Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones

Dharmendra Kumar Tiwari, Ashif Y. Shaikh, Laxmikant S. Pavase, Vikas K. Gumaste, Abdul Rakeeb A S Deshmukh^*

^*Corresponding author af dette arbejde

LUKKET: Natural Products and Peptides

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

19 Citationer (Scopus)

Abstract

Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh₃/CCl₄ reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.

Originalsprog	Engelsk
Tidsskrift	Tetrahedron
Vol/bind	63
Udgave nummer	11
Sider (fra-til)	2524-2534
Antal sider	11
ISSN	0040-4020
DOI	https://doi.org/10.1016/j.tet.2006.12.010
Status	Udgivet - 12 mar. 2007

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Citationsformater

@article{b81a1bc13a2b4a778753e37b85940d38,

title = "Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones",

abstract = "Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.",

keywords = "β-Lactam, Azetidin-2,3-diones, Azetidin-2-ones, Grignard reaction",

author = "Tiwari, {Dharmendra Kumar} and Shaikh, {Ashif Y.} and Pavase, {Laxmikant S.} and Gumaste, {Vikas K.} and Deshmukh, {Abdul Rakeeb A S}",

year = "2007",

month = mar,

day = "12",

doi = "10.1016/j.tet.2006.12.010",

language = "English",

volume = "63",

pages = "2524--2534",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Pergamon Press",

number = "11",

}

TY - JOUR

T1 - Stereoselective synthesis of 3-alkylidene/alkylazetidin-2-ones from azetidin-2,3-diones

AU - Tiwari, Dharmendra Kumar

AU - Shaikh, Ashif Y.

AU - Pavase, Laxmikant S.

AU - Gumaste, Vikas K.

AU - Deshmukh, Abdul Rakeeb A S

PY - 2007/3/12

Y1 - 2007/3/12

N2 - Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.

AB - Azetidin-2,3-diones have been used as synthons for the synthesis of C-3 alkylidene/alkylazetidin-2-ones. Some of the 3-alkylazetidin-2-ones are well known for their cholesterol absorption inhibitor activity. A regio and stereoselective Grignard reaction on a keto group followed by dehydration using PPh3/CCl4 reagent is a key step in this synthesis. Hydrogenation of the 3-alkylideneazetidin-2-ones provided stereoselectively cis-3-alkylazetidin-2-ones in very good yields.

KW - β-Lactam

KW - Azetidin-2,3-diones

KW - Azetidin-2-ones

KW - Grignard reaction

UR - http://www.scopus.com/inward/record.url?scp=33846813846&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.12.010

DO - 10.1016/j.tet.2006.12.010

M3 - Journal article

AN - SCOPUS:33846813846

SN - 0040-4020

VL - 63

SP - 2524

EP - 2534

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -