Catalytic asymmetric dialkynylation reaction of α-dinitrone by utilizing tartaric acid ester as a chiral auxiliary
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Abstract
The asymmetric addition of alkynylzinc reagents, prepared in situ from dimethylzinc and 1-alkynes, to α-dinitrones derived from glyoxal and N-(4-isopropylbenzyl)hydroxylamine was investigated by utilizing dicyclohexyl (R,R)-tartrate as a chiral auxiliary. The addition reaction of methyl(2-phenylethynyl)zinc afforded the corresponding optically active C2-symmetric (R,R)-bis(hydroxylamine) derivative with enantioselectivities of 90% and 81% ee by utilizing a stoichiometric and catalytic amount of the tartrate, respectively. Furthermore, the catalytic addition reaction of several alkynylzinc reagents also furnished the corresponding bis(hydroxylamine) with moderate to good enantioselectivities. © 2008 Elsevier Ltd. All rights reserved.
Journal
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- Tetrahedron Asymmetry
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Tetrahedron Asymmetry 19 (8), 921-931, 2008-05-01
Elsevier
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Details 詳細情報について
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- CRID
- 1390857226428642432
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- NII Article ID
- 120001135615
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- NII Book ID
- AA1074621X
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- ISSN
- 09574166
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- HANDLE
- 2297/9878
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- Text Lang
- en
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- Data Source
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- JaLC
- IRDB
- CiNii Articles
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- Abstract License Flag
- Allowed