Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands

Maria Gabriella Pizzuti; Adriaan J. Minnaard; Ben L. Feringa

doi:10.1021/jo702140f

Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands

Maria Gabriella Pizzuti
, Adriaan J. Minnaard^*
, Ben L. Feringa

^*Corresponding author for this work

Molecular Inorganic Chemistry

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

57 Citations (Scopus)

Abstract

[GRAPHICS]

The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozine and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.

Original language	English
Pages (from-to)	940-947
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	73
Issue number	3
DOIs	https://doi.org/10.1021/jo702140f
Publication status	Published - 1-Feb-2008

Keywords

ALPHA-CHIRAL AMINES
ASYMMETRIC ADDITION
DIORGANOZINC REAGENTS
CONJUGATE ADDITION
ORGANOLITHIUM REAGENTS
DIETHYLZINC ADDITION
N-(DIPHENYLPHOSPHINOYL) IMINES
NUCLEOPHILIC-ADDITION
AMIDOPHOSPHINE LIGAND
ZEROVALENT PALLADIUM

Access to Document

10.1021/jo702140f

http://www.scopus.com/inward/record.url?eid=2-s2.0-38849193449&partnerID=40&md5=d4d6cf52dd4404b83a38cc98413d03cc

Handle.net

Persistent link

Embargoed Document

Catalytic enantioselective addition of organometallic reagents to N-formylimines
Final publisher's version, 144 KB
Request copy

Cite this

@article{64a656d95b2a4258952702eff655b09d,

title = "Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands",

abstract = "[GRAPHICS]The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozine and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99\% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.",

keywords = "ALPHA-CHIRAL AMINES, ASYMMETRIC ADDITION, DIORGANOZINC REAGENTS, CONJUGATE ADDITION, ORGANOLITHIUM REAGENTS, DIETHYLZINC ADDITION, N-(DIPHENYLPHOSPHINOYL) IMINES, NUCLEOPHILIC-ADDITION, AMIDOPHOSPHINE LIGAND, ZEROVALENT PALLADIUM",

author = "Pizzuti, \{Maria Gabriella\} and Minnaard, \{Adriaan J.\} and Feringa, \{Ben L.\}",

note = "Cited By (since 1996): 9",

year = "2008",

month = feb,

day = "1",

doi = "10.1021/jo702140f",

language = "English",

volume = "73",

pages = "940--947",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "AMER CHEMICAL SOC INC",

number = "3",

}

TY - JOUR

T1 - Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands

AU - Pizzuti, Maria Gabriella

AU - Minnaard, Adriaan J.

AU - Feringa, Ben L.

N1 - Cited By (since 1996): 9

PY - 2008/2/1

Y1 - 2008/2/1

N2 - [GRAPHICS]The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozine and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.

AB - [GRAPHICS]The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozine and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.

KW - ALPHA-CHIRAL AMINES

KW - ASYMMETRIC ADDITION

KW - DIORGANOZINC REAGENTS

KW - CONJUGATE ADDITION

KW - ORGANOLITHIUM REAGENTS

KW - DIETHYLZINC ADDITION

KW - N-(DIPHENYLPHOSPHINOYL) IMINES

KW - NUCLEOPHILIC-ADDITION

KW - AMIDOPHOSPHINE LIGAND

KW - ZEROVALENT PALLADIUM

U2 - 10.1021/jo702140f

DO - 10.1021/jo702140f

M3 - Article

SN - 0022-3263

VL - 73

SP - 940

EP - 947

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands

Abstract

Keywords

Access to Document

Handle.net

Embargoed Document

Fingerprint

Cite this