New approaches in asymmetric synthesis using γ-alkoxybutenolides

B.L. Feringa; B de Lange; J.F.G.A. Jansen; J.C. de Jong; M. Lubben; W. Faber; E.P. Schudde

doi:10.1351/pac199264121865

New approaches in asymmetric synthesis using γ-alkoxybutenolides

B.L. Feringa^*, B de Lange, J.F.G.A. Jansen, J.C. de Jong, M. Lubben, W. Faber, E.P. Schudde

^*Corresponding author for this work

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

63 Citations (Scopus)

258 Downloads (Pure)

Abstract

The synthesis of a new class of auxiliary based chiral synthons, γ-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure β-lactam and lignans are given.

Original language	English
Pages (from-to)	1865-1871
Number of pages	7
Journal	Pure and Applied Chemistry
Volume	64
Issue number	12
DOIs	https://doi.org/10.1351/pac199264121865
Publication status	Published - Dec-1992
Event	9TH INTERNATIONAL CONF ON ORGANIC SYNTHESIS - , Canada Duration: 28-Jun-1992 → 2-Jul-1992

Keywords

ENANTIOSELECTIVE SYNTHESIS
1,4-ADDITIONS
MENTHYLOXYBUTENOLIDES
5-ALKOXY-2(5H)-FURANONES
ADDITIONS

Access to Document

10.1351/pac199264121865

Handle.net

Persistent link

Embargoed Document

1992PureApplChemFeringa.PDF
Final publisher's version, 196 KB
Request copy

Cite this

@article{d49b208ff54e4878bf5b600d8362ed6a,

title = "New approaches in asymmetric synthesis using γ-alkoxybutenolides",

abstract = "The synthesis of a new class of auxiliary based chiral synthons, γ-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure β-lactam and lignans are given.",

keywords = "ENANTIOSELECTIVE SYNTHESIS, 1,4-ADDITIONS, MENTHYLOXYBUTENOLIDES, 5-ALKOXY-2(5H)-FURANONES, ADDITIONS",

author = "B.L. Feringa and {de Lange}, B and J.F.G.A. Jansen and {de Jong}, J.C. and M. Lubben and W. Faber and E.P. Schudde",

note = "Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute; 9TH INTERNATIONAL CONF ON ORGANIC SYNTHESIS ; Conference date: 28-06-1992 Through 02-07-1992",

year = "1992",

month = dec,

doi = "10.1351/pac199264121865",

language = "English",

volume = "64",

pages = "1865--1871",

journal = "Pure and Applied Chemistry",

publisher = "Walter de Gruyter GmbH",

number = "12",

}

TY - JOUR

T1 - New approaches in asymmetric synthesis using γ-alkoxybutenolides

AU - Feringa, B.L.

AU - de Lange, B

AU - Jansen, J.F.G.A.

AU - de Jong, J.C.

AU - Lubben, M.

AU - Faber, W.

AU - Schudde, E.P.

N1 - Relation: http://www.rug.nl/scheikunde/ date_submitted:2005 Rights: University of Groningen. Stratingh Institute

PY - 1992/12

Y1 - 1992/12

N2 - The synthesis of a new class of auxiliary based chiral synthons, γ-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure β-lactam and lignans are given.

AB - The synthesis of a new class of auxiliary based chiral synthons, γ-alkoxy-2(5H)-furanones, is described. The multifunctional compounds enter a variety of asymmetric transformations leading to acyclic- and cyclic-products with up to four new stereogenic centers in a single operation with stereoselectivities exceeding 98%. Applications in new routes to an enantiomerically pure β-lactam and lignans are given.

KW - ENANTIOSELECTIVE SYNTHESIS

KW - 1,4-ADDITIONS

KW - MENTHYLOXYBUTENOLIDES

KW - 5-ALKOXY-2(5H)-FURANONES

KW - ADDITIONS

U2 - 10.1351/pac199264121865

DO - 10.1351/pac199264121865

M3 - Article

VL - 64

SP - 1865

EP - 1871

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 12

T2 - 9TH INTERNATIONAL CONF ON ORGANIC SYNTHESIS

Y2 - 28 June 1992 through 2 July 1992

ER -

New approaches in asymmetric synthesis using γ-alkoxybutenolides

Abstract

Keywords

Access to Document

Handle.net

Embargoed Document

Fingerprint

Cite this