Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine

Chen Wei Lin; Sin Wei Liu; Duen Ren Hou

doi:10.1039/c3ob40797g

Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine

Chen Wei Lin, Sin Wei Liu, Duen Ren Hou

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of S _N2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.

Original language	English
Pages (from-to)	5292-5299
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	32
DOIs	https://doi.org/10.1039/c3ob40797g
State	Published - 28 Aug 2013

Access to Document

10.1039/c3ob40797g

Cite this

@article{554d2d22b43d47508727eece2550b440,

title = "Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine",

abstract = "The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of S N2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.",

author = "Lin, {Chen Wei} and Liu, {Sin Wei} and Hou, {Duen Ren}",

year = "2013",

month = aug,

day = "28",

doi = "10.1039/c3ob40797g",

language = "???core.languages.en_GB???",

volume = "11",

pages = "5292--5299",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

number = "32",

}

TY - JOUR

T1 - Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine

AU - Lin, Chen Wei

AU - Liu, Sin Wei

AU - Hou, Duen Ren

PY - 2013/8/28

Y1 - 2013/8/28

N2 - The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of S N2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.

AB - The formation of tetrahydrofurans from 2-hydroxyalkyl-oxirane or aziridine is reported. The 5-endo-tet cyclization/ring opening of aziridine proceeded smoothly to give tetrahydrofurans (THFs) under mild conditions. In contrast, the corresponding process of oxirane was unsuccessful and a sequence of S N2 substitution/cyclization was required to form THFs. The application of the process to prepare ent-(-)-pachastrissamine is described.

UR - http://www.scopus.com/inward/record.url?scp=84880913498&partnerID=8YFLogxK

U2 - 10.1039/c3ob40797g

DO - 10.1039/c3ob40797g

M3 - 期刊論文

C2 - 23835754

AN - SCOPUS:84880913498

SN - 1477-0520

VL - 11

SP - 5292

EP - 5299

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 32

ER -

Formation of tetrahydrofurans via a 5-endo-tet cyclization of aziridines-synthesis of (-)-pachastrissamine

Abstract

Access to Document

Fingerprint

Cite this