Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters

Synlett

Volumn , Issue 5, 2008, Pages 683-686

  Tomooka, Katsuhiko ^a,b   Sakamaki, Junichiro ^b   Harada, Manabu ^b   Wada, Ryoji ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Amines; Asymmetric synthesis; Carbohydrates; Radical reactions; Rearrangements

Indexed keywords

1,2 O CYCLOHEXYLIDENE 5,6 O (DIISOPROPYL)METHYLIDENE ALPHA DEXTRO GLUCOFURANOSE; ALPHA AMINO KETONE; BASE; BENZYLDIMETHYL(ALPHA METHYLPHENACYL)AMMONIUM BROMIDE; CARBOHYDRATE DERIVATIVE; GLUCOSE; KETONE DERIVATIVE; LITHIUM ALKOXIDE; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; RACEMIZATION; STEREOCHEMISTRY; STEVENS REARRANGEMENT;

EID: 41349100524     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032107     Document Type: Article

References (51)

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5. For mechanistic studies of [1,2]-Stevens rearrangement, see: (a) Millard, B. J.; Stevens, T. S. J. Chem. Soc. 1963, 3397.
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9. (a) Recently, Somfai and co-workers reported the first example of enantioselective [2,3]-Stevens rearrangement of allylic ammonium ylide using chiral Lewis acid promoter: Blid, J.; Panknin, O.; Somfai, P. J. Am. Chem. Soc. 2005, 127, 9352.
10. (b) Also, the concomitantly occurred enantioselective [1,2]-Stevens rearrangement has been reported therein.
11. Asymmetric [1,2]-Stevens rearrangement using enantioenriched ammonium ylide has been reported. For the rearrangement with chiral migrating group, see: (a) Campbell, A.; Houston, A. H. J.; Kenyon, J. J. Chem. Soc. 1947, 93.
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21. All the ammonium salts were prepared from the corresponding α-amino ketones and alkyl bromides and purified by recrystallization.
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31. HPLC analysis was carried out on a Chiralcel OD-H column (0.46 x 25 cm) using hexane-i-PrOH (150:1; 0.5 mL/min) as the mobile phase.
32. A rapid racemization of a similar chiral α-amino ketone under weakly basic conditions had been observed; see ref. 5e.
33. 3): = 117.2, 112.7, 105.2, 84.6, 82.1, 75.6, 75.0, 71.2, 36.4, 35.6, 34.4, 33.7, 24.8, 23.8, 23.4, 17.4, 17.2.
34. Similar reactions using alkoxides 3-5 afforded racemic 2b in 16-29% yields.
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46. Significant countercation-effect for enantioselectivity was observed, i.e., the reaction using the corresponding K or Na alkoxide of 8 afforded only the racemic 2b in moderate yields.
47. The enantioselectivity significantly decreased (18% ee), when one equivalent of 8 was used.
48. The corresponding alcohols of 10, 11, and 13 have been reported: (a) For 10, see: Einhorn, C.; Luche, J. Carbohydr. Res. 1986, 155, 258.
49. (b) For 11, see: Luboradzki, R.; Pakulski, Z.; Sartowska, B. Tetrahedron 2005, 61, 10122.
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51. 4, filtered, and the solvent was removed in vacuo. The residue was purified by silica gel chromatography to afford the α-amino ketone (S)-2b (7.0 mg, 91%, 61% ee) and recovered 14a (103 mg, 99%).