Silver-sensitive enantioselectivity in asymmetric Heck reactions

Michael C. McDermott; G. Richard Stephenson; Andrew J. Walkington

doi:10.1055/s-2006-958447

Silver-sensitive enantioselectivity in asymmetric Heck reactions

Michael C. McDermott, G. Richard Stephenson, Andrew J. Walkington

Chemistry of Materials and Catalysis

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

15 Citations (Scopus)

Abstract

Amine- and pure Ag(I)-promoted asymmetric Heck cyclisations of 2-iodobut-2-enanilide 1 both gave the oxindole product (R)-(+)-2 in relatively low ee but the partial reduction of the silver salt promoted a substantially more stereocontrolled route to (S)-(-)-2 in a reaction in which the use of Strem Atg(3)PO(4) gave the R-product and Aldrich Ag3PO4 gave the S-product.

Original language	English
Pages (from-to)	51-54
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2006-958447
Publication status	Published - 2007

Access to Document

10.1055/s-2006-958447

Cite this

@article{55c35a25da7f42cf90d5e1dfafedc930,

title = "Silver-sensitive enantioselectivity in asymmetric Heck reactions",

abstract = "Amine- and pure Ag(I)-promoted asymmetric Heck cyclisations of 2-iodobut-2-enanilide 1 both gave the oxindole product (R)-(+)-2 in relatively low ee but the partial reduction of the silver salt promoted a substantially more stereocontrolled route to (S)-(-)-2 in a reaction in which the use of Strem Atg(3)PO(4) gave the R-product and Aldrich Ag3PO4 gave the S-product.",

author = "McDermott, {Michael C.} and Stephenson, {G. Richard} and Walkington, {Andrew J.}",

note = "McDermott, Michael C. Stephenson, G. Richard Walkington, Andrew J.",

year = "2007",

doi = "10.1055/s-2006-958447",

language = "English",

pages = "51--54",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - Silver-sensitive enantioselectivity in asymmetric Heck reactions

AU - McDermott, Michael C.

AU - Stephenson, G. Richard

AU - Walkington, Andrew J.

N1 - McDermott, Michael C. Stephenson, G. Richard Walkington, Andrew J.

PY - 2007

Y1 - 2007

N2 - Amine- and pure Ag(I)-promoted asymmetric Heck cyclisations of 2-iodobut-2-enanilide 1 both gave the oxindole product (R)-(+)-2 in relatively low ee but the partial reduction of the silver salt promoted a substantially more stereocontrolled route to (S)-(-)-2 in a reaction in which the use of Strem Atg(3)PO(4) gave the R-product and Aldrich Ag3PO4 gave the S-product.

AB - Amine- and pure Ag(I)-promoted asymmetric Heck cyclisations of 2-iodobut-2-enanilide 1 both gave the oxindole product (R)-(+)-2 in relatively low ee but the partial reduction of the silver salt promoted a substantially more stereocontrolled route to (S)-(-)-2 in a reaction in which the use of Strem Atg(3)PO(4) gave the R-product and Aldrich Ag3PO4 gave the S-product.

U2 - 10.1055/s-2006-958447

DO - 10.1055/s-2006-958447

M3 - Article

SN - 0936-5214

SP - 51

EP - 54

JO - Synlett

JF - Synlett

IS - 1

ER -