Exceptionally high felkin-AnH control for the addition of nucleophiles to a β-aminocyclopropylcarbaldehyde

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 4985-4988

  Bubert, Christian ^a   Reiser, Oliver ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CRYSTAL STRUCTURE; DIASTEREOISOMER; STEREOSPECIFICITY; X RAY ANALYSIS;

EID: 0030847955     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01065-4     Document Type: Article

References (29)

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6. (a) Houben Weyl: Methods in Organic Chemistry Vol. 17a-e, de Meijere, A. (Ed), Thieme: Stuttgart 1997,
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20. (d) Paulini, K.; Reißig, H.-U. Liebigs Ann. Chem. 1994, 549-554.
21. Voigt, J.; Noltemeyer, M.; Reiser, O. Synlett 1997, 202-204.
22. All products are racemic, for clarity only one enantiomer is shown. 4 can also be obtained enantiomerically pure by enzymatic resolution: C. Cabrele, T. Stauch, O. Vielhauer, M. Pietsch, O. Reiser, unpublished results.
23. Tammy, S. R.; Grossmann, J.; Fowler, F. J. Am. Chem. Soc. 1972, 94, 6495-6501.
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26. tBu) and of 6c and by NOE experiments on 8 which was readily obtained from 6a,b and 6e-g by deformylation and cyclization with 2-methoxypropene. The stereochemistry of 6d was confirmed by its transformation to 6c. (Formula Presented)
27. c, 1'-H), 8.04 (s, OCHO); 6g: 1.89 (dd, J = 5.4, 3.7 Hz, 1-H), 8.00 (s, OCHO).
28. Atomic coordinates, bond lengths and angels, and thermal parameters of 5 can be obtained on request from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ (UK).
29. Bubert, C.; Voigt, J.; Biasetton, S.; Reiser, O. Synlett 1994, 675-677.