Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH)

Karen Patricia Smith; Fei Liu

Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH)

Karen Patricia Smith, Fei Liu

Department of Molecular Sciences

Research output: Chapter in Book/Report/Conference proceeding › Other chapter contribution

Abstract

MBH is an atom efficient reaction that provides densely functionalised adducts and generates a chiral centre [1,2]. The reaction can be extremely slow and is highly substrate dependant. An appropriately positioned protic functional group within the catalyst is essential for enantioselectivity. Our aim is to establish the catalytic activity of a series of chiral [2’-diphenylphosphinoyl-[1,1]-binaphthyl] amine derivatives for the Morita-Baylis-Hillman reaction. Two synthetic approaches will be evaluated starting with 2,2’dibromo-1,1-binaphthyl; amine functionality will be introduced either through a Buchwald-Harwig [4] strategy or an intermolecular Staudinger [5] reaction.

Original language	English
Title of host publication	Proceedings of the NZIC 2006
Subtitle of host publication	back to the basics : from small molecules to materials and surfaces
Editors	Matthias Lein
Place of Publication	Rotorua, New Zealand
Publisher	The New Zealand Institute of Chemistry
Pages	86-87
Number of pages	2
Volume	II
ISBN (Print)	9780473118549
Publication status	Published - 2006
Event	New Zealand Institute of Chemistry Conference - Rotorua, New Zealand Duration: 2 Dec 2006 → 6 Dec 2006

Conference

Conference	New Zealand Institute of Chemistry Conference
City	Rotorua, New Zealand
Period	2/12/06 → 6/12/06

Cite this

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title = "Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH)",

abstract = "MBH is an atom efficient reaction that provides densely functionalised adducts and generates a chiral centre [1,2]. The reaction can be extremely slow and is highly substrate dependant. An appropriately positioned protic functional group within the catalyst is essential for enantioselectivity. Our aim is to establish the catalytic activity of a series of chiral [2{\textquoteright}-diphenylphosphinoyl-[1,1]-binaphthyl] amine derivatives for the Morita-Baylis-Hillman reaction. Two synthetic approaches will be evaluated starting with 2,2{\textquoteright}dibromo-1,1-binaphthyl; amine functionality will be introduced either through a Buchwald-Harwig [4] strategy or an intermolecular Staudinger [5] reaction.",

author = "Smith, {Karen Patricia} and Fei Liu",

year = "2006",

language = "English",

isbn = "9780473118549",

volume = "II",

pages = "86--87",

editor = "Matthias Lein",

booktitle = "Proceedings of the NZIC 2006",

publisher = "The New Zealand Institute of Chemistry",

note = "New Zealand Institute of Chemistry Conference ; Conference date: 02-12-2006 Through 06-12-2006",

}

Smith, KP & Liu, F 2006, Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH). in M Lein (ed.), Proceedings of the NZIC 2006: back to the basics : from small molecules to materials and surfaces. vol. II, The New Zealand Institute of Chemistry, Rotorua, New Zealand, pp. 86-87, New Zealand Institute of Chemistry Conference, Rotorua, New Zealand, 2/12/06.

Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH). / Smith, Karen Patricia; Liu, Fei.

Proceedings of the NZIC 2006: back to the basics : from small molecules to materials and surfaces. ed. / Matthias Lein. Vol. II Rotorua, New Zealand : The New Zealand Institute of Chemistry, 2006. p. 86-87.

Research output: Chapter in Book/Report/Conference proceeding › Other chapter contribution

TY - CHAP

T1 - Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH)

AU - Smith, Karen Patricia

AU - Liu, Fei

PY - 2006

Y1 - 2006

N2 - MBH is an atom efficient reaction that provides densely functionalised adducts and generates a chiral centre [1,2]. The reaction can be extremely slow and is highly substrate dependant. An appropriately positioned protic functional group within the catalyst is essential for enantioselectivity. Our aim is to establish the catalytic activity of a series of chiral [2’-diphenylphosphinoyl-[1,1]-binaphthyl] amine derivatives for the Morita-Baylis-Hillman reaction. Two synthetic approaches will be evaluated starting with 2,2’dibromo-1,1-binaphthyl; amine functionality will be introduced either through a Buchwald-Harwig [4] strategy or an intermolecular Staudinger [5] reaction.

AB - MBH is an atom efficient reaction that provides densely functionalised adducts and generates a chiral centre [1,2]. The reaction can be extremely slow and is highly substrate dependant. An appropriately positioned protic functional group within the catalyst is essential for enantioselectivity. Our aim is to establish the catalytic activity of a series of chiral [2’-diphenylphosphinoyl-[1,1]-binaphthyl] amine derivatives for the Morita-Baylis-Hillman reaction. Two synthetic approaches will be evaluated starting with 2,2’dibromo-1,1-binaphthyl; amine functionality will be introduced either through a Buchwald-Harwig [4] strategy or an intermolecular Staudinger [5] reaction.

M3 - Other chapter contribution

SN - 9780473118549

VL - II

SP - 86

EP - 87

BT - Proceedings of the NZIC 2006

A2 - Lein, Matthias

PB - The New Zealand Institute of Chemistry

CY - Rotorua, New Zealand

T2 - New Zealand Institute of Chemistry Conference

Y2 - 2 December 2006 through 6 December 2006

ER -

Synthesis and design of bifunctional phosphine catalysts for the asymmetric Morita Baylis Hillman reaction (MBH)

Abstract

Conference

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