Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 29, Pages 9005-9010Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200109
Keywords
amines; enantioselectivity; hydroamination; hydrogenation; iron
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Funding
- State of Mecklenburg-Western Pomerania
- BMBF
- DFG
- Evonik Foundation
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Enantiomerically pure chiral amines are of increasing importance and commercial value in the fine chemical, pharmaceutical, and agrochemical industries. Here, we describe the straightforward synthesis of chiral amines by combining the atom-economic and environmentally friendly hydroamination of alkynes with an enantioselective hydrogenation of in situ generated imines by using inexpensive hydrogen. By following this novel approach, a wide range of terminal alkynes can be reductively hydroaminated with primary amines including alkyl-, and arylalkynes as well as aryl and heteroaryl amines. Excellent yields and selectivities up to 94?% ee and 96?% isolated yield were obtained.
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