Stereoselective synthesis of Threo 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-propan-1-ol

Holzforschung

Volumn 51, Issue 2, 1997, Pages 169-172

  Collier, W E ^a   Fisher, T H ^a   Schultz, T P ^a,b  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

^b FOREST PRODUCTS LABORATORY   (United States)

Author keywords

Diastereomers; Erythro (S,R R,S) O 4 dilignol; Lignin models; Oxazaborolidine; Reduction; Threo (S,S R,R) O 4 dilignol

Indexed keywords

EID: 0345629179     PISSN: 00183830     EISSN: None     Source Type: Journal    
DOI: 10.1515/hfsg.1997.51.2.169     Document Type: Article

References (15)

1. Adler, E., S. Delin and G.E. Miksche. 1966. Synthese des Isoeu-genolgylkol-β-(2-Methoxyphenyl)-Äthers. Acta Chem. Scand. 20: 1035-1037.
2. Brunow, G., L. Koskinen and P. Urpilainen. 1981. Reversal of the direction of asymmetric induction in the borohydride reduction of two propiophenone derivatives using a polymer-bound reagent. Acta Chem. Scand. B35: 53-54.
3. Brunow, G., J. Sipila, K. Lundquist and S. Unger. 1988. The preparation of threo forms of β-O-4 type lignin model compounds. Cellulose Chem. Tech. 22: 191-199.
4. Corey, E.J., R.K. Bakshi and S. Shibata. 1987a. Highly enantioseiective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. J. Am. Chem. Soc. 109: 5551-5553.
5. Corey, E.J., R.K. Bakshi, S. Shibata, C.-P. Chen and V.K. Singh. 1987b. A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep synthesis J. Am. Chem. Soc. 109: 7925-7926.
6. Gierer J and I. Norén. 1962a. Zur Spaltung von β-Hydroxy-Al-kyl-Aryläthern durch Alkali. II. Der stereochemische Verlauf. Acta Chem. Scand. 16: 1976-1988.
7. Gierer J. and I. Norén. 1962b. Über die Reaktionen des Lignins bei der Sulfatkochung. II. Modellversuche zur Spaltung von Aryl-Alkylätherbindungen durch Alkali. Acta Chem. Scand. 16: 1713-1729.
8. Hubbard Jr., T.F., T.P. Schultz and T.H. Fisher. 1992. Alkaline hydrolysis of nonphenolic β-0-4 lignin model dimers: Substituent effects on the leaving phenoxide in neighboring group vs direct nucleophilic attack. Holzforschung 46: 315-320.
9. Kratzl, K. and M. Oburger. 1980. Kondensationsreaktionen von Lignin-Modellsubstanzen mit Phenol unter saurer Katalyse. Holzforschung 34: 11-16.
10. Miksche, G.E. 1972. Zum alkalischen Abbau der p-Alkoxy-Arylglycerin-β-Arylätherstrukturen des Lignins. Versuche mit erythro-Veratrylglycerin-β-Guajacyläther. Acta Chem. Scand. 26: 3275-3281.
11. Obst J.R. 1983. Kinetics of alkaline cleaveage of β-aryl ether bonds in lignin models: Significance to delignification. Holzforschung 37: 23-28.
12. Ralph J. 1982. Reactions of lignin model quinone methides and NMR studies of lignins. Ph.D. Dissertation. Univ. of Wisconsin-Madison, U.S.A., Univ. Microfilm No. 82-26987.
13. Ralph. J. 1993. Personal communication. Received August 29th, 1995
14. Ralph J and R.F. Helm. 1991. Rapid proton NMR method for determination of threo:erythro ratios in lignin model compounds and examination of reduction stereochemistry. J. Agric. Food Chem. 39: 705-709.
15. Samuels, W.D., D.A. Nelson and R.T. Hallen. 1986. The influence of a-aryl ethers on the asymmetric reduction of carbonyls. Tetrahed. Lett. 27: 3091-3094.