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

Forskningsoutput: Tidskriftsbidrag › Artikel › Vetenskaplig › Peer review

13 Citeringar (Scopus)

Sammanfattning

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.

Originalspråk	Odefinierat/okänt
Sidor (från-till)	5305–5307
Antal sidor	3
Tidskrift	Tetrahedron Letters
Volym	50
Nummer	38
DOI	https://doi.org/10.1016/j.tetlet.2009.06.136
Status	Publicerad - 2009
MoE-publikationstyp	A1 Tidskriftsartikel-refererad

Nyckelord

Allylation
Asymmetric synthesis
Conjugate addition
Ring-closing metathesis
Spirocyclic ether

Åtkomst av dokument

10.1016/j.tetlet.2009.06.136

Citera det här

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

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.",

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author = "S Rosenberg and Reko Leino",

year = "2009",

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

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

volume = "50",

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journal = "Tetrahedron Letters",

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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 -