Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediols via enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2429-2432

  Lee, Namkyu ^a   Kim, Young Woo ^a   Chang, Kieyoung ^a   Kim, Key H ^a   Jew, Sang Sup ^b   Kim, Dae Kee ^a  

^a Sunkyong Industries   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BUTANEDIOL;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029968096     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00310-3     Document Type: Article

References (11)

1. (a) Kaneko, T.; Katsura, H.; Asano, H.; Wakabayashi, K. Chem. Ind. 1960, 1187.
2. (b) Poss, A. J.; Smyth, M. S. Tetrahedron Lett. 1987, 28, 5469.
3. Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org. Chem. 1989, 54, 2471.
4. Jansen, J. F. G. A.; Feringa, B. L. Tetrahedron Lett. 1989, 30, 5481.
5. Bourguignon, J. J.; Wermuth, C. G. J. Org. Chem. 1981, 46, 4889.
6. (a) Taylor, R. J. K. Synthesis 1985, 364.
7. (b) Cahiez, G.; Alami, M. Tetrahedron 1989, 45, 4163.
8. de Jong, J. C.; Bolhuis, F.; Feringa, B. L. Tetrahedron:Asymmetry 1991, 2, 1247.
9. 2O using a Dean-Stark trap afforded a mixture of 2a and its diastereomer in 90 % yield after vacuum distillation. Diastereomerically pure 2a was obtained in 59 % yield after single crystallization with petroleum ether (4.5 L) at -20 °C. Epimerization of the mother liquor in the presence of a catalytic amount of p-TsOH followed by crystallization afforded an additional amount of diastereomerically pure 2a (9 %).
10. Tomioka, K.; Mizuguchi, H.; Koga, K. Chem. Pharm. Bull. 1982, 30, 4304.
11. D +3.11 ° (c 3.18, MeOH).