Process for the diastereoselective reductive pinacol coupling of

Details Process for the diastereoselective reductive pinacol coupling of Process for the diastereoselective reductive pinacol coupling of

1994-06-13

1996-05-21

Russel, Jeffrey E.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Peptides containing saccharide radicals, e.g., bleomycins, etc.

530338, 530339, C07K 102

Patent

active

055191134

ABSTRACT:
Process for the diastereoselective reductive pinacol coupling of homochiral .alpha.-aminoaldehydes
A process for the preparation of optically pure symmetrical compounds of the formula I ##STR1## is described, in which R.sup.1, R.sup.2 and R.sup.3, are explained in the description, with simultaneous control of the four centers of chirality indicated by *.

REFERENCES:
Morrison and Boyd, Organic Chemistry, 4th Ed. Chapter 30, pp. 1117-1120 (1983).
A. W. Konradi et al., "Synthesis of 3-Amino-1,2-Diols Via the Cross Pinacol Coupling of N-Protected .alpha.-Amino Aldehydes and Aliphatic Aldehydes Using [V.sub.2 Cl.sub.3 (THF).sub.6 ].sub.2 [Zn.sub.2 Cl.sub.6 ]," Abstracts of the 199th Meeting of the American Chemical Society, Apr. 22-27, 1990, ORGN 409.
D. J. Kempf et al., "Structure-Based, C.sub.2 Symmetric Inhibitors of HIV Protease," J. Med. Chem., 1990, 33, 2687-2689.
A. W. Konradi et al., "Pinacol Homocoupling of (S)-2-[N-(Benzyloxy-carbonyl)amino] Aldehydes by [V.sub.2 Cl.sub.3 (THF).sub.6 ].sub.2 [Zn.sub.2 Cl.sub.6 ]. Synthesis of C.sub.2 -Symmetric (1S,2R,3R,4S)-1,4-Diamino 2,3-Diols," J. Org. Chem., 1992.
A. W. Konradi et al., Journal of Organic Chemistry, vol. 55, pp. 4506-4508 (1990).
P. M. Takahara et al., Tetrahedron Letters, vol. 30, No. 51, pp. 7177-7180 (1989).
J. H. Freudenberger et al., Journal of the American Chemical Society, vol. 111, pp. 8014-8016 (1989).

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