Pinacol rearrangement for constructing asymmetric centers adjacent to heterocycles

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 6937-6940

  Shinohara, Tomoichi ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALUMINUM DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ELECTRON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PINACOL REARRANGEMENT; STEREOSPECIFICITY;

EID: 0037163255     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01626-X     Document Type: Article

References (42)

1. Asymmetric synthesis of indolmycin: (a) Takeda, T.; Mukaiyama, T. Chem. Lett. 1980, 163; (b) Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323; (c) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111; (d) Hasuoka, A.; Nakayama, Y.; Adachi, M.; Kamiguchi, H.; Kamiyama, K. Chem. Pharm. Bull. 2001, 49, 1604. Synthesis of (±)-indolmycin: (e) Dhue, Y.-K. Tetrahedron Lett. 1996, 37, 6447.
2. Asymmetric synthesis of indolmycin: (a) Takeda, T.; Mukaiyama, T. Chem. Lett. 1980, 163; (b) Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323; (c) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111; (d) Hasuoka, A.; Nakayama, Y.; Adachi, M.; Kamiguchi, H.; Kamiyama, K. Chem. Pharm. Bull. 2001, 49, 1604. Synthesis of (±)-indolmycin: (e) Dhue, Y.-K. Tetrahedron Lett. 1996, 37, 6447.
3. Asymmetric synthesis of indolmycin: (a) Takeda, T.; Mukaiyama, T. Chem. Lett. 1980, 163; (b) Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323; (c) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111; (d) Hasuoka, A.; Nakayama, Y.; Adachi, M.; Kamiguchi, H.; Kamiyama, K. Chem. Pharm. Bull. 2001, 49, 1604. Synthesis of (±)-indolmycin: (e) Dhue, Y.-K. Tetrahedron Lett. 1996, 37, 6447.
4. Asymmetric synthesis of indolmycin: (a) Takeda, T.; Mukaiyama, T. Chem. Lett. 1980, 163; (b) Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323; (c) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111; (d) Hasuoka, A.; Nakayama, Y.; Adachi, M.; Kamiguchi, H.; Kamiyama, K. Chem. Pharm. Bull. 2001, 49, 1604. Synthesis of (±)-indolmycin: (e) Dhue, Y.-K. Tetrahedron Lett. 1996, 37, 6447.
5. Asymmetric synthesis of indolmycin: (a) Takeda, T.; Mukaiyama, T. Chem. Lett. 1980, 163; (b) Akita, H.; Kawaguchi, T.; Enoki, Y.; Oishi, T. Chem. Pharm. Bull. 1990, 38, 323; (c) Bando, T.; Shishido, K. Heterocycles 1997, 46, 111; (d) Hasuoka, A.; Nakayama, Y.; Adachi, M.; Kamiguchi, H.; Kamiyama, K. Chem. Pharm. Bull. 2001, 49, 1604. Synthesis of (±)-indolmycin: (e) Dhue, Y.-K. Tetrahedron Lett. 1996, 37, 6447.
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27. All new compounds were fully characterized by spectroscopic means and combustion analysis.
28. 3-Indolyllithium and 3-benzofuranyllithium were generated by halogen-lithium exchange of the corresponding bromide (n-BuLi, THF, -78°C, 1 min) 2-Thienyllithium, 2-benzothiophenyllithium, 2-benzofuranyllithium, and 5-methoxy-2-benzofuranyllithium were generated by hydrogen-lithium exchange (n-BuLi, THF, -78→25°C, 30 min) 1-Methyl-2-indolyllithium was generated by hydrogen-lithium exchange in the presence of TMEDA (n-BuLi, THF, -78→25°C, 30 min).
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30. 5a,b we previously employed will be disclosed elsewhere.
31. An authentic sample of (±)-7a was prepared from (±)-ethyl lactate along the same lines.
32. 12a
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35. The (R) absolute configuration of the alcohol center was deduced by the Mosher-Kusumi method based on the chemical shifts of the corresponding (+)- and (-)-MTPA esters. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512; (b) Kusumi, T.; Ohtani, I.; Inoue, Y.; Kakisawa, H. Tetrahedron Lett. 1988, 29, 4731.
36. The (R) absolute configuration of the alcohol center was deduced by the Mosher-Kusumi method based on the chemical shifts of the corresponding (+)- and (-)-MTPA esters. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512; (b) Kusumi, T.; Ohtani, I.; Inoue, Y.; Kakisawa, H. Tetrahedron Lett. 1988, 29, 4731.
37. The enantiomeric excess was determined as follows. For 7b: ketone 7b was reduced with DIBAL to give the diastereomeric alcohols (ca. 1/1), which were converted to the corresponding (+)-MTPA esters. For comparison, the alcohols derived from (±)-ethyl lactate were converted to the (+)-MTPA esters. For 7c-f: by the chiral HPLC analysis (DAICEL CHIRALCEL OD-H, i-PrOH/hexane=1/9) of the chiral ketones and (±)-ketones.
38. 1H NMR, and the configurations of alcoholic center are based on the analogy with 8a.
39. 3Al was used as the second Lewis acid instead, the yield was somewhat lower, and some byproducts were produced, including the one from ethylation of the aldehyde intermediate.
40. The enantiomeric excess was determined by the chiral HPLC analysis (DAICEL CHIRALCEL OD-H, i-PrOH/hexane=1/9).
41. D value of the corresponding methyl ester 18 was compared with that of 18 reported by Takeda (Ref. 1a).
42. An authentic sample of (±)-18 was prepared from (±)-ethyl lactate along the same lines.