Trifluoroacetyl-Activated Nitrogen−Nitrogen Bond Cleavage of Hydrazines by Samarium(II) Iodide
摘要:
Trifluoroacetyl derivatives of hydrazines undergo clean and efficient reductive cleavage of the N-N bond with SmI2 in the presence of MeOH. After N-trifluoroacetylation, acyl-, aryl-, and alkyl-substituted hydrazines are reductively cleaved by this method to afford trifluoroacetamides in yields ranging from 70 to 96%. These conditions accommodate alkene functionality, avoid racemization, and furnish chiral amines bearing a readily removable TFA protecting group.
BF3-promoted hydrostannation of N-heteroatom-substituted imines for the reduction of CN bond
摘要:
Hydrostannation of n-heteroatom-substituted imines such as oxime ethers, hydrazones, oximes, nitrones, and V-sulfonyl imines using a combination of Bu3SnH and (BF3OEt2)-O-. has been systematically studied. Not only aromatic aldimines but also kitimines and aliphatic imines were reduced to give the corresponding amines. (C) 2002 Elsevier Science Ltd. All rights reserved.
Hydrostannation of n-heteroatom-substituted imines such as oxime ethers, hydrazones, oximes, nitrones, and V-sulfonyl imines using a combination of Bu3SnH and (BF3OEt2)-O-. has been systematically studied. Not only aromatic aldimines but also kitimines and aliphatic imines were reduced to give the corresponding amines. (C) 2002 Elsevier Science Ltd. All rights reserved.
Trifluoroacetyl-Activated Nitrogen−Nitrogen Bond Cleavage of Hydrazines by Samarium(II) Iodide
作者:Hui Ding、Gregory K. Friestad
DOI:10.1021/ol036480r
日期:2004.2.1
Trifluoroacetyl derivatives of hydrazines undergo clean and efficient reductive cleavage of the N-N bond with SmI2 in the presence of MeOH. After N-trifluoroacetylation, acyl-, aryl-, and alkyl-substituted hydrazines are reductively cleaved by this method to afford trifluoroacetamides in yields ranging from 70 to 96%. These conditions accommodate alkene functionality, avoid racemization, and furnish chiral amines bearing a readily removable TFA protecting group.