A new entry to asymmetric synthesis of optically active α,γ-substituted γ-butyrolactones, using a carbohydrate derived amide as both a chiral auxiliary and a proton source

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 529-532

  Huang, Ling Lin ^a   Xu, Ming Hua ^a   Lin, Guo Qiang ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; PROTONS; REACTION KINETICS; STEREOCHEMISTRY;

CHIRAL AUXILIARY; PROTON SOURCES; STEREOSELECTIVE CONTROL;

AROMATIC HYDROCARBONS;

4 METHOXYACETOPHENONE; CARBOHYDRATE; GAMMA BUTYROLACTONE; KETONE; METHACRYLIC ACID; PROTON; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; ISOMER; NONHUMAN; STEREOCHEMISTRY;

4-BUTYROLACTONE; AMIDES; MOLECULAR STRUCTURE; OPTICAL ROTATION; PROTONS; STEREOISOMERISM;

EID: 12344302937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485637     Document Type: Article

References (25)

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10. For γ-butyrolactones, see: (a) Depre, D.; Chen, L.-Y.; Ghosez, L. Tetrahedron 2003, 59, 6797. (b) McMahon, L. R.; Coop, A.; France, C. P.; Winger, G.; Woolverton, W. L. Eur. J. Pharmacol. 2003, 466, 113. (c) Katoh, T.; Nishide, K.; Node, M.; Hiroo, O. Heterocycles 1999, 50, 833. (d) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. J. Org. Chem. 1998, 63, 2385.
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18. Isomannide and isosorbide are easily obtained by dehydration of mannitol and sorbitol, respectively. (a) Wiggins, L. F. J. Chem. Soc. 1945, 4. (b) Montgomery, R.; Wiggins, L. F. J. Chem. Soc. 1946, 390.
19. Isomannide and isosorbide are easily obtained by dehydration of mannitol and sorbitol, respectively. (a) Wiggins, L. F. J. Chem. Soc. 1945, 4. (b) Montgomery, R.; Wiggins, L. F. J. Chem. Soc. 1946, 390.
20. The recovery of the chiral auxiliary was examined in this case, and 86% of the employed auxiliary was recovered by column chromatography.
21. Proposed working models are included in the Supporting Information.
22. Prepared from D-glucose, see: (a) Tian, H.; She, X.; Shi, Y. J. Org. Chem. 2002, 67, 2435. (b) Shu, L.; Shen, Y.-M.; Burke, C.; Goeddel, D.; Shi, Y. J. Org. Chem. 2003, 68, 4963.
23. Prepared from D-glucose, see: (a) Tian, H.; She, X.; Shi, Y. J. Org. Chem. 2002, 67, 2435. (b) Shu, L.; Shen, Y.-M.; Burke, C.; Goeddel, D.; Shi, Y. J. Org. Chem. 2003, 68, 4963.
24. The difference between the trans/cis ratio in entry 3 and that in entry 5 might be explained by the conformation change of the reaction transition state in the diluted system. The exact reason is not clear at this time.
25. Other experimental results that are also supportive: comparing with the results in entry 5 of Table 1, no significant difference was found (trans/cis = 69/31, 99% ee for trans and 79% ee for cis) when substrate 4b was reacted with 4′-methoxyacetophenone (5) in the presence of 1.0 equiv of tert-butyl alcohol under diluted (5 times) conditions.