ISSN:
0947-6539
Keywords:
asymmetric synthesis
;
cycloadditions
;
imines
;
lactams
;
silicon
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3-amino-4-alkyl-β-lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl- and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β-lactam antibiotic building blocks.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970030909
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