Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 3, Issue 8, Pages 851-855Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201402077
Keywords
alpha-silyl amines; copper; imines; ketimines; N-heterocyclic carbenes
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Funding
- Tsinghua-Peking Joint Centers for Life Sciences (CLS)
- National Natural Science Foundation of China [21371107]
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We developed an efficient and enantioselective method for the synthesis of chiral alpha-silyl amines. In the presence of a copper(I)-chiral monodentate N-heterocyclic carbene complex (5 mol%), smooth nucleophilic silicon transfer from Me(2)PhSiBpin (pin = pinacolato) to tosyl-protected aldimines affords the corresponding alpha-silyl amines in 77-93% yields over 15 examples and satisfactory ee of 79-99%. The asymmetric silylation of ketimines was also explored.
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