Shioiri

The procedure described is essentially that of Shioiri and Yamada. Diphenyl phosphorazidate is a useful and versatile reagent in organic synthesis. It has been used for racemlzatlon-free peptide syntheses, thiol ester synthesis, a modified Curtius reaction, an esterification of a-substituted carboxylic acld, formation of diketoplperazines, alkyl azide synthesis, phosphorylation of alcohols and amines,and polymerization of amino acids and peptides. - Furthermore, diphenyl phosphorazidate acts as a nitrene source and as a 1,3-dipole.An example in the ring contraction of cyclic ketones to form cycloalkanecarboxylic acids is presented in the next procedure, this volume. 

Yamada, S. Hamada, Y. Ninomiya, K. Shioiri, T. Tetrahedron Lett. 1976, 4749 see following procedure, this volume. 

Submitted by Yasumasa Hamada and Takayuki Shioiri -. Checked by M. F. Semmelhack and E. Spiess. 

N. Hashimoto, T. Aoyama, andT. Shioiri, Chem. Pharm. Bull, 29, 1475 (1981). 

Hamada, Y, K. Ando, and T. Shioiri. Chsim Rhcyim Hull. 29, 25S MS81J. 

Hamarla, Y, K. Anrlo, andT. Shioiri. Chsm Ehanm Suit.. 29, 259 0961 . 

K. Mikami, S. Matsukawa, J. Am. Chem. Soc. 115, 7039 (1993) see also S. Kobayashi. I. Hachiya, J. Org. Chem. 57. 1324 (1992). Relatively moderate enantioselectivity is reached in Mukaivama-type aldol additions which are catalyzed by A-bcnzylcinchonium fluoride A. Ando, T. Miura, T. Tatematsu. T. Shioiri, Tetrahedron Lett. 34, 1507 (1993). 

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