Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation

Rob Hoen; Theodora Tiemersma-Wegman; Barbara Procuranti; Laurent Lefort; Johannes G. de Vries; Adriaan J. Minnaard; Ben L. Feringa

doi:10.1039/b615131k

Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation

Rob Hoen, Theodora Tiemersma-Wegman, Barbara Procuranti, Laurent Lefort, Johannes G. de Vries, Adriaan J. Minnaard^*, Ben L. Feringa

^*Corresponding author for this work

Synthetic Organic Chemistry

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

61 Citations (Scopus)

416 Downloads (Pure)

Abstract

A series of protected beta(2)-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained ( up to 91%) with full conversion for a number of beta-amino acids.

Original language	English
Pages (from-to)	267-275
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	5
Issue number	2
DOIs	https://doi.org/10.1039/b615131k
Publication status	Published - 2007

Keywords

MONODENTATE P-LIGANDS
BETA-AMINO ACIDS
TRANSITION-METAL CATALYSIS
ASYMMETRIC HYDROGENATION
COMBINATORIAL APPROACH
OLEFIN-HYDROGENATION
PHOSPHORAMIDITE LIGANDS
STEREOSELECTIVE-SYNTHESIS
ABSOLUTE-CONFIGURATION
PHOSPHORUS LIGANDS

Access to Document

10.1039/b615131k

2007OrgBiomolChemHoen.pdfFinal publisher's version, 236 KB

http://www.scopus.com/inward/record.url?eid=2-s2.0-33846104860&partnerID=40&md5=d8d5ed5dcea90b66797866c742598d89

Handle.net

Persistent link

Cite this

@article{6fbefb430f524efbb231f6a0e48a95b7,

title = "Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation",

abstract = "A series of protected beta(2)-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained ( up to 91%) with full conversion for a number of beta-amino acids.",

keywords = "MONODENTATE P-LIGANDS, BETA-AMINO ACIDS, TRANSITION-METAL CATALYSIS, ASYMMETRIC HYDROGENATION, COMBINATORIAL APPROACH, OLEFIN-HYDROGENATION, PHOSPHORAMIDITE LIGANDS, STEREOSELECTIVE-SYNTHESIS, ABSOLUTE-CONFIGURATION, PHOSPHORUS LIGANDS",

author = "Rob Hoen and Theodora Tiemersma-Wegman and Barbara Procuranti and Laurent Lefort and {de Vries}, {Johannes G.} and Minnaard, {Adriaan J.} and Feringa, {Ben L.}",

year = "2007",

doi = "10.1039/b615131k",

language = "English",

volume = "5",

pages = "267--275",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "ROYAL SOC CHEMISTRY",

number = "2",

}

TY - JOUR

T1 - Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation

AU - Hoen, Rob

AU - Tiemersma-Wegman, Theodora

AU - Procuranti, Barbara

AU - Lefort, Laurent

AU - de Vries, Johannes G.

AU - Minnaard, Adriaan J.

AU - Feringa, Ben L.

PY - 2007

Y1 - 2007

N2 - A series of protected beta(2)-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained ( up to 91%) with full conversion for a number of beta-amino acids.

AB - A series of protected beta(2)-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained ( up to 91%) with full conversion for a number of beta-amino acids.

KW - MONODENTATE P-LIGANDS

KW - BETA-AMINO ACIDS

KW - TRANSITION-METAL CATALYSIS

KW - ASYMMETRIC HYDROGENATION

KW - COMBINATORIAL APPROACH

KW - OLEFIN-HYDROGENATION

KW - PHOSPHORAMIDITE LIGANDS

KW - STEREOSELECTIVE-SYNTHESIS

KW - ABSOLUTE-CONFIGURATION

KW - PHOSPHORUS LIGANDS

U2 - 10.1039/b615131k

DO - 10.1039/b615131k

M3 - Article

SN - 1477-0520

VL - 5

SP - 267

EP - 275

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 2

ER -

Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this