Asymmetric cyclopentannelation. Chiral auxiliary on the allene

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2447-2450

  Harrington, Paul E ^a   Tius, Marcus A ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

CYCLOPENTANES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0034632362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0001362     Document Type: Article

References (22)

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3. This area has been reviewed: (a) Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336-358.
4. (b) Reissig, H.-U. Angew. Chem., Int. Ed. Engl. 1992, 31, 288-290. See also:
5. (a) Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197-1207.
6. (b) Chika, J-i.: Takei, H. Tetrahedron Lett. 1998, 39, 605-608.
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9. (e) Chiappe, C.; Moro, G. L.; Munforte, P. Tetrahedron: Asymmetry 1997, 8, 2311-2317.
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12. Bollenback, G. N. In Methods in Carbohydrate Chemistry; Whistler, R. L., Wolfram, M. L., Eds.; Academic Press: New York, 1963; Vol. 2, pp 326-328.
13. Bessodes, M.; Shamsazar, J.; Antonakis, K. Synthesis 1988, 560-562.
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17. The enantioselectivities were determined by HPLC on a Daicel Chiralcel OD (250 mm x 10 mm) chiral column with mixtures of 2-propanol and hexanes as eluant, with a flow rate of 1 mL/min with UV detection at 254 nm; co-injection with racemate confirmed the peak assignment in the chromatogram.
18. Harrington, P. E.; Tius, M. A. Org. Lett. 1999, 1, 649-651.
19. Amides 10, 14, and 16 were prepared by Horner-Emmons condensation of the corresponding aldehydes with triethyl 2-phosphonopropionate followed by conversion to the amide; see: Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171-4174. Amides 8, 12, 18. and 20 were prepared from the corresponding commercially available acids via the acid chlorides.
20. 4). Purification by flash column chromatography on silica (5% EtOAc in hexanes) gave cyclopentenone 7 (32 mg, 52% yield, 68% ee) as a colorless oil.
21. Ichikawa, J.; Fujiwara, M.; Okauchi, T.; Minami, T. Synlett 1998, 927-929.
22. 3).