Mild and efficient synthesis of 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose: Precursor of the first carbohydrate-derived chiral Mn(III)-salen complex

Tetrahedron

Volumn 58, Issue 50, 2002, Pages 10065-10071

  Yan, Shanhong ^a   Klemm, Dieter ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

(salen)manganese(III) complexes; Asymmetric reactions; Carbohydrate; Diamino sugars; Enantiomeric epoxidations; Jacobsen's catalyst; Mn(III) salen catalysts

Indexed keywords

5,6 DIAMINO 5,6 DIDEOXY 1,2 O ISOPROPYLIDENE 3 O METHYL BETA LEVO IDOFURANOSE; ALKENE; CARBOHYDRATE; FURAN DERIVATIVE; GLUCOSE; HYPOCHLORITE SODIUM; MANGANESE; NAPHTHALENE DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037049285     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01294-2     Document Type: Article

References (12)

1. Zhang W., Loebach J.L., Wilson S.R., Jacobsen E.N. J. Am. Chem. Soc. 112:1990;2801-2803.
2. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
3. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
4. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
5. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
6. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
7. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
8. Recent reviews: (a) Katsuki T. Curr. Org. Chem. 5:2001;663-678 (b) Canali L., Sherrington D.C. Chem. Soc. Rev. 28:1999;85-93 (c) Ito Y.N., Katsuki T. Bull. Chem. Soc. Jpn. 72:1999;603-619 (d) Linker T. Angew. Chem., Int. Ed. Engl. 36:1997;2060-2062 (e) Katsuki T. J. Mol. Catal. A: Chem. 113:1996;87-107 (f) Jacobsen E.N. Abel E.W., Stone F.G.A., Wilkinson G., Comprehensive Organometallic Chemistry II. Vol. 12:1995;Pergamon, New York. Chapter 11.1 (g) Katsuki T. Coord. Chem. Rev. 140:1995;189-214.
9. Allen J.R., Ensign S.A. Biochemistry. 38:1999;247-256.
10. Calinaud P., Gelas J. Synthesis of Isopropylidene, Benzylidene, and Related Acetals. Hanessian S., Preparative Carbohydrate Chemistry. 1997;3-33 Marcel Dekker, New York.
11. Bessodes M., Shamsazar J., Antonakis K. Synthesis. 1998;560-562.
12. Hanson J. J. Chem. Educ. 78:2001;1266-1268.