Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 7, Pages 1612-1617Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00047b
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Funding
- JSPS KAKENHI [JP15J05294, JP25460004]
- Uehara Memorial Foundation
- Naito Foundation
- Grants-in-Aid for Scientific Research [17K08205, 17H03969, 15J05294] Funding Source: KAKEN
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The transfer of axial chirality of allenes is beginning to be exploited as a powerful method for creating central chirality, particularly through the use of transition metal catalysis. In this communication, the transfer of axial chirality of chiral allenes via nickel-catalysed hydrocyanation is achieved through both regio- and face-selective hydronickelation as well as regioselective reductive elimination. This protocol was applied to 12 substrates and gave chiral carbonitriles with up to 97% ee. Further application to hydrocyanative cyclization using a chiral allene-yne is also presented, along with a discussion of the corresponding mechanism of racemization.
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