Ring-closing metathesis as a tool for the efficient preparation of chiral spirocyclic ethers from homoallylic alcohols

S Rosenberg; Reko Leino

doi:10.1016/j.tetlet.2009.06.136

Ring-closing metathesis as a tool for the efficient preparation of chiral spirocyclic ethers from homoallylic alcohols

S Rosenberg, Reko Leino

Tutkimustuotos: Lehtiartikkeli › Artikkeli › Tieteellinen › vertaisarvioitu

12 Sitaatiot (Scopus)

Abstrakti

The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.

Alkuperäiskieli	Ei tiedossa
Sivut	5305–5307
Sivumäärä	3
Julkaisu	Tetrahedron Letters
Vuosikerta	50
Numero	38
DOI - pysyväislinkit	https://doi.org/10.1016/j.tetlet.2009.06.136
Tila	Julkaistu - 2009
OKM-julkaisutyyppi	A1 Julkaistu artikkeli, soviteltu

Keywords

Allylation
Asymmetric synthesis
Conjugate addition
Ring-closing metathesis
Spirocyclic ether

Pääsy asiakirjaan

10.1016/j.tetlet.2009.06.136

Viittausmuodot

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abstract = "The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "Allylation, Asymmetric synthesis, Conjugate addition, Ring-closing metathesis, Spirocyclic ether, Allylation, Asymmetric synthesis, Conjugate addition, Ring-closing metathesis, Spirocyclic ether, Allylation, Asymmetric synthesis, Conjugate addition, Ring-closing metathesis, Spirocyclic ether",

author = "S Rosenberg and Reko Leino",

year = "2009",

doi = "10.1016/j.tetlet.2009.06.136",

language = "Odefinierat/ok{\"a}nt",

volume = "50",

pages = "5305–5307",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "38",

}

TY - JOUR

T1 - Ring-closing metathesis as a tool for the efficient preparation of chiral spirocyclic ethers from homoallylic alcohols

AU - Rosenberg, S

AU - Leino, Reko

PY - 2009

Y1 - 2009

N2 - The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.

AB - The preparation of chiral spirocyclic ethers via allylic etherification/olefin metathesis of homoallylic alcohols is investigated. This reaction sequence transforms the enantiopure substrate alcohols, synthesized by a one-pot asymmetric rhodium-catalyzed conjugate addition/metal-mediated allylation procedure, into the desired spite ethers with full conversions and in excellent isolated yields. The synthetic sequence provides an efficient means for a rapid construction of functionalized spiro ethers in a stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.

KW - Allylation

KW - Asymmetric synthesis

KW - Conjugate addition

KW - Ring-closing metathesis

KW - Spirocyclic ether

KW - Allylation

KW - Asymmetric synthesis

KW - Conjugate addition

KW - Ring-closing metathesis

KW - Spirocyclic ether

KW - Allylation

KW - Asymmetric synthesis

KW - Conjugate addition

KW - Ring-closing metathesis

KW - Spirocyclic ether

U2 - 10.1016/j.tetlet.2009.06.136

DO - 10.1016/j.tetlet.2009.06.136

M3 - Artikel

SN - 0040-4039

VL - 50

SP - 5305

EP - 5307

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -