SN2 displacement at the quaternary carbon center: A novel entry to the synthesis of α,α-disubstituted α-amino acids This Letter is dedicated to the late Professor Harry Wasserman, a great chemist as well as a splendid artist

Tetrahedron Letters

Volumn 56, Issue 23, 2015, Pages 3169-3171

  Ishihara, Kotaro ^a   Hamamoto, Hiromi ^a   Matsugi, Masato ^a   Shioiri, Takayuki ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

Azidation; Bis(p nitrophenyl)phosphorazidate; Quaternary carbon center; SN2 displacement; tert alcohols; , Disubstituted amino acids

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; AZIDE; CARBON; ESTER;

AMINO ACID SYNTHESIS; ARTICLE; CATALYSIS; CHIRALITY; HYDROGENATION; PROTEIN QUATERNARY STRUCTURE; SUBSTITUTION REACTION;

EID: 84929574032     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.01.041     Document Type: Article

References (6)

1. T. Mukaiyama, K. Kuroda, Y. Maruyama, and Y. Hayashi Chem. Lett. 37 2008 1072
2. T. Mukaiyama, K. Kuroda, and Y. Maruyama Heterocycles 80 2010 63
3. J.E. Green, D.M. Bender, S. Jackson, M.J. O'Donnell, and J.M. McCarthy Org. Lett. 11 2009 807 and references therein
4. For a review, see T. Shioiri Wako Junyaku Jiho 73 2005 6
5. M. Mizuno, and T. Shioiri Chem. Commun. 1997 2165 and references therein
6. 2DPPA is easily prepared by the nitration of DPPA (T. Shioiri, and S. Yamada Chem. Pharm. Bull. 22 1974 855), and now commercially available from Wako Pure Chemical Industries, Japan