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For reviews, see: (a)
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For reviews, see: (a) Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164.
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Jurczak, J.1
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(e)
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(e) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
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Reetz, M.T.1
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Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141-1143.
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Reetz, M.T.1
Drewes, M.W.2
Schmitz, A.3
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0026353381
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Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939-6942.
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J. Org. Chem.
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Denis, J.-N.1
Correa, A.2
Greene, A.E.3
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12
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0000285544
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For other examples of N-protected phenylglycinal derivatives, see: (a)
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For other examples of N-protected phenylglycinal derivatives, see: (a) Matsunaga, N.; Harada, H.; Aoyama, T.; Shioiri, T. Heterocycles 1992, 33, 235-255.
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Heterocycles
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Matsunaga, N.1
Harada, H.2
Aoyama, T.3
Shioiri, T.4
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14
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0030018805
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(c)
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(c) Andres, J. M.; Barrio, R.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. J. Org. Chem. 1996, 61, 4210-4213.
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(1996)
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Andres, J.M.1
Barrio, R.2
Martinez, M.A.3
Pedrosa, R.4
Perez-Encabo, A.5
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15
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0026669060
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For comparison of the TEMPO and Swern procedures, see:
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Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032. For comparison of the TEMPO and Swern procedures, see: Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051-6064.
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Tetrahedron Lett.
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Leanna, M.R.1
Sowin, T.J.2
Morton, H.E.3
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16
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0032575218
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Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032. For comparison of the TEMPO and Swern procedures, see: Jurczak, J.; Gryko, D.; Kobrzycka, E.; Gruza, H.; Prokopowicz, P. Tetrahedron 1998, 54, 6051-6064.
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(1998)
Tetrahedron
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Jurczak, J.1
Gryko, D.2
Kobrzycka, E.3
Gruza, H.4
Prokopowicz, P.5
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17
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0343775206
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For a prior example employing sodium borohydride in the reduction of phenylglycinal derivatives, see Ref. 6
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For a prior example employing sodium borohydride in the reduction of phenylglycinal derivatives, see Ref. 6.
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18
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0033546262
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Frigerio, M.; Santagostino M.; Sputore S.J.
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2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol
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2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
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(1999)
Org. Chem.
, vol.64
, pp. 4537-4538
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19
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33751384984
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2-Iodoxybenzoic acid was prepared by oxidation of 2-iodobenzoic acid according to a recently reported procedure: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538. 2-Iodoxybenzoic acid was transformed to the Dess-Martin periodinane following the Ireland protocol: Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
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(1993)
, vol.58
, pp. 2899
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Ireland, R.E.1
Liu, L.J.2
Org., Chem.3
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21
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0001755016
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The superiority of the Dess-Martin periodinane for the preparation of chiral α-fluoro aldehydes has been documented:
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The superiority of the Dess-Martin periodinane for the preparation of chiral α-fluoro aldehydes has been documented: Davis, F. A.; Kasu, P. V. N.; Sundarababu, G.; Qi, H. J. Org. Chem. 1997, 62, 7546-7547.
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(1997)
J. Org. Chem.
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Davis, F.A.1
Kasu, P.V.N.2
Sundarababu, G.3
Qi, H.4
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22
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0002203331
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(a)
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(a) Garst, M. E.; Bonfiglio, J. N.; Grudoski, D. A.; Marks, J. Tetrahedron Lett. 1978, 30, 2671-2674.
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(1978)
Tetrahedron Lett.
, vol.30
, pp. 2671-2674
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Garst, M.E.1
Bonfiglio, J.N.2
Grudoski, D.A.3
Marks, J.4
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23
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0001026255
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(b)
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(b) Garst, M. E.; Bonfiglio, J. N.; Grudoski, D. A.; Marks, J. J. Org. Chem. 1980, 45, 2307-2315.
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J. Org. Chem.
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Garst, M.E.1
Bonfiglio, J.N.2
Grudoski, D.A.3
Marks, J.4
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24
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0001587747
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For leading references, see: Gross, E.; Meienhofer, J., Eds.; Academic: New York Chapter 7.
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For leading references, see: Kemp, D. S. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic: New York, 1979; Volume 1, Chapter 7.
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(1979)
In the Peptides
, vol.1
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Kemp, D.S.1
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25
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0019947041
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For the preparation of N-Boc and N-Cbz alaninal in ees ranging from 82-99%, using TEMPO, Swern, or Parikh-Doering oxidations, see: Ref. 8, and
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For the preparation of N-Boc and N-Cbz alaninal in ees ranging from 82-99%, using TEMPO, Swern, or Parikh-Doering oxidations, see: Ref. 8, and Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921-1924.
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(1982)
Chem. Pharm. Bull.
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, pp. 1921-1924
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Hamada, Y.1
Shioiri, T.2
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26
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0342469993
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Note
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R(N-Fmoc-(R)-phenylglycinol)=24.5 min) established an ee of 99%.
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