ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α-Substituted N-acylbornane-10, 2-sultams 6, 9, and 10 can be converted into enantiomerically pure ketones 5. 13, and 14, respectively, via a two-step procedure involving a known mercaptolysis reaction followed by an [Fe(acac)3]-mediated coupling of the resulting S-benzyl thioesters with Grignard reagents. Furthermore, enantiomerically pure aldehydes 23 can be obtained from α-substituted N-acylbornane-10,2-sultams 6 via a one-step reduction with (i-Bu)2AIH. No epimerization at the α-chiral center is observed during the cleavage reaction whereby the chiral auxiliary, bornane-10,2-sultam 1 or ent-l, was recovered. By using this methodology, several natural products or precursors thereof can be prepared.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19970800502
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