A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination

Nils Meyer; Peter W. Roesky

doi:10.1021/om060440k

A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination

Nils Meyer, Agustino, Peter W. Roesky

Department of Chemistry

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

85 Citations (Scopus)

Abstract

The enantiomerically pure bridged aminotroponiminate S,S-H ₂{(iPrATI)₂diph}, in which two aminoisopropyl-troponimine moieties are linked by 1,2-(S,S)-diamino-1,2-diphenylethane, has been prepared. The chiral lutetium alkyl complex of composition [(R,R)-{(iPrATI) ₂diphLuCH₂SiMe₃(THF)] (3) was obtained via two synthetic approaches. In the first approach the dipotassium salt [(S,S)-K ₂{(iPrATI)₂-diph}] (1) of the ligand was reacted via a salt metathesis with lutetium trichloride to give [(S,S)-{(iPrATI) ₂diph}LuCl(THF)] (2). Reaction of 2 with LiCH₂SiMe ₃ resulted in 3. Compound 3 can also be obtained by the reaction of [Lu(CH₂SiMe₃)₃(THF)₂] with (S,S)-H₂[(iPrATI)₂diph} under elimination of Me ₄Si. The alkyl complex 3 was used as catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins. Good catalytic activities and moderate enantioselectivties were observed.

Original language	English
Pages (from-to)	4179-4182
Number of pages	4
Journal	Organometallics
Volume	25
Issue number	17
DOIs	https://doi.org/10.1021/om060440k
Publication status	Published - 14 Aug 2006

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@article{5a1baa342f2242d3859ebecede581e5f,

title = "A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination",

abstract = "The enantiomerically pure bridged aminotroponiminate S,S-H 2{(iPrATI)2diph}, in which two aminoisopropyl-troponimine moieties are linked by 1,2-(S,S)-diamino-1,2-diphenylethane, has been prepared. The chiral lutetium alkyl complex of composition [(R,R)-{(iPrATI) 2diphLuCH2SiMe3(THF)] (3) was obtained via two synthetic approaches. In the first approach the dipotassium salt [(S,S)-K 2{(iPrATI)2-diph}] (1) of the ligand was reacted via a salt metathesis with lutetium trichloride to give [(S,S)-{(iPrATI) 2diph}LuCl(THF)] (2). Reaction of 2 with LiCH2SiMe 3 resulted in 3. Compound 3 can also be obtained by the reaction of [Lu(CH2SiMe3)3(THF)2] with (S,S)-H2[(iPrATI)2diph} under elimination of Me 4Si. The alkyl complex 3 was used as catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins. Good catalytic activities and moderate enantioselectivties were observed.",

author = "Nils Meyer and Agustino and Roesky, {Peter W.}",

year = "2006",

month = aug,

day = "14",

doi = "10.1021/om060440k",

language = "English",

volume = "25",

pages = "4179--4182",

journal = "Organometallics",

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T1 - A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination

AU - Meyer, Nils

AU - Agustino, null

AU - Roesky, Peter W.

PY - 2006/8/14

Y1 - 2006/8/14

N2 - The enantiomerically pure bridged aminotroponiminate S,S-H 2{(iPrATI)2diph}, in which two aminoisopropyl-troponimine moieties are linked by 1,2-(S,S)-diamino-1,2-diphenylethane, has been prepared. The chiral lutetium alkyl complex of composition [(R,R)-{(iPrATI) 2diphLuCH2SiMe3(THF)] (3) was obtained via two synthetic approaches. In the first approach the dipotassium salt [(S,S)-K 2{(iPrATI)2-diph}] (1) of the ligand was reacted via a salt metathesis with lutetium trichloride to give [(S,S)-{(iPrATI) 2diph}LuCl(THF)] (2). Reaction of 2 with LiCH2SiMe 3 resulted in 3. Compound 3 can also be obtained by the reaction of [Lu(CH2SiMe3)3(THF)2] with (S,S)-H2[(iPrATI)2diph} under elimination of Me 4Si. The alkyl complex 3 was used as catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins. Good catalytic activities and moderate enantioselectivties were observed.

AB - The enantiomerically pure bridged aminotroponiminate S,S-H 2{(iPrATI)2diph}, in which two aminoisopropyl-troponimine moieties are linked by 1,2-(S,S)-diamino-1,2-diphenylethane, has been prepared. The chiral lutetium alkyl complex of composition [(R,R)-{(iPrATI) 2diphLuCH2SiMe3(THF)] (3) was obtained via two synthetic approaches. In the first approach the dipotassium salt [(S,S)-K 2{(iPrATI)2-diph}] (1) of the ligand was reacted via a salt metathesis with lutetium trichloride to give [(S,S)-{(iPrATI) 2diph}LuCl(THF)] (2). Reaction of 2 with LiCH2SiMe 3 resulted in 3. Compound 3 can also be obtained by the reaction of [Lu(CH2SiMe3)3(THF)2] with (S,S)-H2[(iPrATI)2diph} under elimination of Me 4Si. The alkyl complex 3 was used as catalyst in the intramolecular hydroamination reaction of nonactivated terminal aminoolefins. Good catalytic activities and moderate enantioselectivties were observed.

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JO - Organometallics

JF - Organometallics

IS - 17

ER -

A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination

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