Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3713-3716

  Shing, Tony K M ^a   Chow, Hak Fun ^a   Chung, Ivan H F ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0029944030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00648-X     Document Type: Article

References (22)

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12. Uemura, M.; Hayashi, Y.; Hayashi, Y. Tetrahedron Asymmetry, 1993, 4, 2291. For asymmetric Diels-Alder reactions with chiral acyl iron complex, see Davies, S. G.; Walker, J. C. J. Chem. Soc., Chem. Commun. 1986, 609.
13. The corresponding molybdenum and tungsten tricarbonyl complexes were less stable and did not survive the subsequent transformations. It is noteworthy that all the metal tricarbonyl complexes of the corresponding benzyl glycoside 1 were unstable and not amenable as chiral auxiliaries.
14. The convenient complexation procedure described by Professor Davies was applied to our case: see Blagg, J.; Davies, S. G.; Holman, N. J.; Laughton, C. A.; Mobbs, B. E. J. Chem. Soc., Perkin Trans I 1986, 1581.
15. 4C1 solution. The resulting mixture was filtered through a pad of silica gel and washed with EtOAc (10 mL). The filtrate was concentrated in vacuo to give a crude yellow syrup that was purified by flash column chromatography on silica gel to afford the cycloadducts.
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18. The absolute configuration of the major cycloadduct 10 derived from the reaction between furan and was determined by conversion into the known alcohol 11: see (a) Kunstmann, M. P.; Tarbell, D. S.; Autrey R. L. J. Am. Chem. Soc., 1962, 84, 4115;
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