Aluminum-catalyzed enantio- and diastereoselective carbonyl addition of propargylsilanes. A new approach to enantioenriched vinyl epoxides

Journal of the American Chemical Society

Volumn 129, Issue 31, 2007, Pages 9606-9607

  Evans, David A ^a   Aye, Yimon ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM; CARBONYL DERIVATIVE; EPOXIDE; SILANE DERIVATIVE; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DERIVATIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; MOLECULAR STABILITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 34547725857     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0740420     Document Type: Article

References (18)

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4. (b) Niimi, L.; Shiino, K.; Hiraoka, S.; Yokozawa T. Tetrahedron Lett. 2001, 42, 1721.
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8. Evans, D. A.; Aye, Y. J. Am. Chem. Soc. 2006, 128, 11034.
9. All propargylsilanes in this study were synthesized from commercially available prop-2-ynol in three steps (see Supporting Information).
10. See cif files in Supporting Information.
11. Smadja, W. Chem. Rev. 1983, 83, 263.
12. 3 returned 66% ee, 15% yield (at 0°C), and 14% ee, 5% yield, respectively.
13. Results using catalyst 1b: 90% ee, 19% yield (R = Et); 91% ee, 13% yield (R = n-pent).
14. 2AlOTf led to decomposition pathways.
15. Vinyl epoxide was recovered intact under the following conditions: TBAF, THF (reflux), AcOH (neat, up to 100°C), HF·pyridine (room temp).
16. 2DNOESY analysis. VanBrunt, M. P.; Standaert, R. F. Org. Lett. 2000, 2, 705.
17. 2Si 12.
18. 2, bromination of the phenyl rings was observed instead.