Journal
TETRAHEDRON LETTERS
Volume 53, Issue 2, Pages 119-122Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.11.002
Keywords
t-Butanesulfinyl imine; Grignard reagent; Addition; Diastereoconvergent; Carbohydrate
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Funding
- National Natural Science Foundation of China [20602008, 20832005, 21072032]
- IBS (Fudan University)
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Unexpected high levels of diastereoconvergence (dr >15:1) were observed in the addition of a series of Grignard reagents in THF to D-xylose-derived t-BS aldimines 2a,b affording (S-S,5R)- and (R-S,5R)-adducts. This anomaly was absent when using ethereal solutions of organometallic reagents, revealing the subtle solvent effects. This study illustrates the scope and limitations of N-t-BS imine chemistry in complex systems. (C) 2011 Elsevier Ltd. All rights reserved.
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