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

Tetrahedron Letters

Volumn 51, Issue 48, 2010, Pages 6298-6300

  Nishigaichi, Yutaka ^a   Fujimoto, Takahiro ^a   Takuwa, Akio ^a   Iwamoto, Hidetoshi ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

1,4 Aminoalcohol derivatives; Allyltin; Asymmetric induction; Lewis acid; Sulfonylimine

Indexed keywords

1,4 AMINO ALCOHOL DERIVATIVE; AMINOALCOHOL; FUNCTIONAL GROUP; IMINE; LEWIS ACID; N SULFONYLIMINE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 78049402524     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.104     Document Type: Article

References (24)

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14. Hereafter, the configuration of the chiral center derived from the racemic tin reagent 1 is shown as R for simplicity and it is described as R.
15. 4 with 3 equiv of diethyl ether to suppress transmetallation.
16. 4, and condensed under reduced pressure. The residue was chromatographed on a silica gel TLC to isolate the product.
17. 9
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22. CCDC 791980 contains the supplementary crystallographic data for this Letter. 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.
23. 3) δ (multiplicity, J/Hz, integration): (S,R)-syn-adduct (R = Ph) 7.64 (dd, 8.4, 1.2, 2H), 7.44 (t, 7.6, 1H), 7.32 (t, 8.1, 2H), 7.13-7.18 (m, 5H), 5.52 (d, 4.6, 1H), 5.07 (s, 1H), 4.92 (q, 6.6, 1H), 4.77 (s, 1H), 4.52 (ddd, 9.0, 5.4, 4.6, 1H), 2.95 (br s, 3H), 2.93 (br s, 3H), 2.51 (dd, 15.0, 5.4, 1H), 2.37 (dd, 15.0, 9.0, 1H), 1.22 (d, 6.6, 3H). (R,R)-anti-adduct (R = Ph) 7.64 (d, 8.5, 2H), 7.39 (t, 7.3, 1H), 7.28 (t, 8.3, 2H), 7.11-7.10 (m, 3H), 7.01-7.04 (m, 2H), 6.60 (d, 7.3, 1H), 5.08 (q, 6.1, 1H), 4.97 (s, 1H), 4.67 (q, 6.3, 1H), 4.39 (s, 1H), 2.98 (br s, 3H), 2.96 (br s, 3H), 2.46-2.48 (m, 2H), 1.26 (d, 6.3, 3H).
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