Binary 1,4-asymmetric induction from a single allyltin reagent with a chiral nitrogen functional group toward aldehydes

Tetrahedron Letters

Volumn 49, Issue 13, 2008, Pages 2124-2127

  Nishigaichi, Yutaka ^a   Tamura, Ken ichi ^a   Ueda, Narifumi ^a   Iwamoto, Hidetoshi ^a   Takuwa, Akio ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALLYLTIN REAGENT; NITROGEN; REAGENT; STANNIC CHLORIDE; TIN DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; DIASTEREOISOMER; SYNTHESIS; X RAY ANALYSIS;

EID: 39649097618     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.112     Document Type: Article

References (24)

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16. 4-promoted reaction with an amido-allyltin reagent:. Tanaka K., Yoda H., Isobe Y., and Kaji A. J. Org. Chem. 51 (1986) 1856
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18. CCDC 671467 and 671468 contain the supplementary crystallographic data for this Letter (syn-8b and anti-4, respectively). These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
19. 4-mediated reactions of 2a and of 6 may be attributed to the cyclic structure of the imido moiety, of which coordination would cause steric strain. Thus, a different transition state should be adopted.
20. 1H NMR spectra: syn-4a, 1.27 (3H, d, J = 6.8 Hz), 2.30 (1H, dd, J = 13.9, 9.5 Hz), 2.54 (1H, dd, J = 14.0, 3.3 Hz), 3.46 (1H, br, OH), 3.68 (3H, s), 4.22-4.33 (1H, m), 4.85-4.89 (1H, m), 4.94 (1H, br, NH), 5.02 (1H, s), 5.14 (1H, s), 7.22-7.39 (5H, m). anti-4a, 1.25 (3H, d, J = 6.8 Hz), 2.44 (2H, d, J = 6.8 Hz), 3.55 (1H, br, OH), 3.64 (3H, s), 4.21-4.30 (1H, m), 4.92 (1H, br, NH), 4.95 (1H, s), 5.11 (1H, s), 5.28-5.32 (1H, m), 7.22-7.39 (5H, m).
21. 4, condensed, and chromatographed to isolate the product.
22. 3 (0.2 mmol) were added an aldehyde (0.2 mmol) in ether (2 mL) and 2 (0.3 mmol) in ether (2 mL) at room temperature under nitrogen with stirring. After 12 h, the reaction mixture was worked up as above.
23. 4-mediated reaction of 2 b resulted in poor diastereoselectivity; nearly equal amounts of syn- and anti-adducts were obtained.
24. Considerable decomposition of 2c proceeded with most of the aldehyde intact.