Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding a-methylamino acid products

Stephanie Oerum; Peter Krabbe; Magnus Schau-Magnussen; Søren Furbo; Jesper Bendix; Anders Hammershøi

doi:10.1039/c2dt32250a

Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding a-methylamino acid products

Stephanie Oerum, Peter Krabbe, Magnus Schau-Magnussen, Søren Furbo, Jesper Bendix, Anders Hammershøi

1 Citationer (Scopus)

Abstract

Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L₄Co(O ₂CCHNCH₃)]²⁺ [L₄ = (en)₂ (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-R_C*-S_N*)- [Co(en)₂(O₂CCH[CH₂NO₂]NHCH ₃)]ZnCl₄ and rac-(Δ*-R_C*- S_N*)-[Co(en)₂(O₂CCH[CH ₂COCH₃]NHCH₃)]ZnCl₄, were established by X-ray diffraction.

Originalsprog	Engelsk
Tidsskrift	Dalton Transactions (Print Edition)
Vol/bind	42
Udgave nummer	1
Sider (fra-til)	292-298
Antal sider	7
ISSN	1477-9226
DOI	https://doi.org/10.1039/c2dt32250a
Status	Udgivet - 7 jan. 2013

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10.1039/c2dt32250a

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title = "Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding a-methylamino acid products",

abstract = "Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L4Co(O 2CCHNCH3)]2+ [L4 = (en)2 (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-RC*-SN*)- [Co(en)2(O2CCH[CH2NO2]NHCH 3)]ZnCl4 and rac-(Δ*-RC*- SN*)-[Co(en)2(O2CCH[CH 2COCH3]NHCH3)]ZnCl4, were established by X-ray diffraction.",

author = "Stephanie Oerum and Peter Krabbe and Magnus Schau-Magnussen and S{\o}ren Furbo and Jesper Bendix and Anders Hammersh{\o}i",

year = "2013",

month = jan,

day = "7",

doi = "10.1039/c2dt32250a",

language = "English",

volume = "42",

pages = "292--298",

journal = "Acta chemica Scandinavica. Series A: Physical and inorganic chemistry",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding a-methylamino acid products

AU - Oerum, Stephanie

AU - Krabbe, Peter

AU - Schau-Magnussen, Magnus

AU - Furbo, Søren

AU - Bendix, Jesper

AU - Hammershøi, Anders

PY - 2013/1/7

Y1 - 2013/1/7

N2 - Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L4Co(O 2CCHNCH3)]2+ [L4 = (en)2 (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-RC*-SN*)- [Co(en)2(O2CCH[CH2NO2]NHCH 3)]ZnCl4 and rac-(Δ*-RC*- SN*)-[Co(en)2(O2CCH[CH 2COCH3]NHCH3)]ZnCl4, were established by X-ray diffraction.

AB - Highly stereoselective and rapid (<1 min) addition reactions to the imine double bond of 2-(methylimino)acetate complexes [L4Co(O 2CCHNCH3)]2+ [L4 = (en)2 (7), (tren) (11)] were achieved in aqueous solution with nitromethane, ethyl 3-oxobutanoate or diethyl malonate. The molecular structures of two product complexes, rac-(Δ*-RC*-SN*)- [Co(en)2(O2CCH[CH2NO2]NHCH 3)]ZnCl4 and rac-(Δ*-RC*- SN*)-[Co(en)2(O2CCH[CH 2COCH3]NHCH3)]ZnCl4, were established by X-ray diffraction.

U2 - 10.1039/c2dt32250a

DO - 10.1039/c2dt32250a

M3 - Journal article

C2 - 23168834

SN - 1477-9226

VL - 42

SP - 292

EP - 298

JO - Acta chemica Scandinavica. Series A: Physical and inorganic chemistry

JF - Acta chemica Scandinavica. Series A: Physical and inorganic chemistry

IS - 1

ER -

Highly stereoselective, cobalt(III)-directed Mannich additions in water yielding a-methylamino acid products

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