N-Acetylbornane-10,2-sultam: A Useful, Enantiomerically Pure Acetate Synthon for Asymmetric Aldol Reactions

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6397-6400

  Bond, Silas ^a   Perlmutter, Patrick ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000634244     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961953b     Document Type: Article

References (24)

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12. The use of 1 equiv each of diethylboron triflate and diisopropylethylamine gave identical stereoselection but with significant quantities of unchanged starting material.
13. In response to a referee's suggestion we prepared purified diethylboron triflate (see ref 15) and repeated several of the reactions listed in Table 1. In all cases, the results were, within experimental error, the same as those obtained using diethylboron triflate generated "in situ". This precludes the possibility of ethylboron ditriflate being responsible for our results (see Boeckman, R. K., Jr.; Johnson, A. T.; Musselman, R. A. Tetrahedron Lett. 1994, 35, 8521-8524).
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21. For examples of Lewis-acid promoted anti-aldol reactions which would be expected to provide the opposite stereochemical result at the newly-formed carbinol center to those described here see: Raimundo, B. C.; Heathcock, C. H. Synlett 1995, 1213-1214 and references cited therein.
22. Bartlett, P. D.; Knox, L. H. Organic Synthesis; John Wiley and Sons: New York, 1973; Collect. Vol. V; pp 196-198.
23. Davis, F. A.; Towson, J. C.; Weismiller, M. C.; Lal, S.; Carroll, P. J. J. Am. Chem. Soc. 1988, 110, 8477-8482.
24. The author has deposited atomic coordinates for this structure with the Cambridge Cristallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.