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Phosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocks

Author:
Oña Burgos, Pascual; Fernández de las Nieves, Ignacio; Iglesias Valdés-Solís, María José; García-Granda, SantiagoUniovi authority; López Ortiz, Fernando
Publication date:
2008
Publisher version:
http://dx.doi.org/10.1021/ol7028096
Citación:
Organic Letters, 10 (4), p. 537-540 (2008); doi:10.1021/ol7028096
Descripción física:
p. 537-540
Abstract:

N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P−N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.

N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P−N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.

URI:
http://hdl.handle.net/10651/10820
ISSN:
1523-7060
Identificador local:

1099

DOI:
10.1021/ol7028096
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