STEREOSELECTIVE SYNTHESES OF ERYTHRO-BETA-AMINO AND THREO-BETA-AMINO ALCOHOL DERIVATIVES VIA HETERO-DIELS-ALDER REACTIONS

The reaction of 1,3-dimethoxy-1-[(trimethylsilyl)oxy]butadiene with a variety of N-protected .alpha.-amino aldehydes under the influence of Lewis acid has been studied. The reaction provides an .alpha.,.beta.-unsaturated lactone that is useful in further transformations. When N-tert-butoxycarbonyl-p...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 111; no. 12; pp. 4368 - 4371
Main Authors MIDLAND, MM, AFONSO, MM
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 07.06.1989
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:The reaction of 1,3-dimethoxy-1-[(trimethylsilyl)oxy]butadiene with a variety of N-protected .alpha.-amino aldehydes under the influence of Lewis acid has been studied. The reaction provides an .alpha.,.beta.-unsaturated lactone that is useful in further transformations. When N-tert-butoxycarbonyl-protected amino aldehydes are used with diethylaluminum chloride or tris-[3-[(heptafluoropropyl)hydroxymethylene]camphorato]europium(III) as a catalyst, the reaction provides a diastereomer consistant with a chelation-controlled process. Diastereometric ratios range from 80:20 (alaninal) to 95:5 (valinal). This stereochemistry is dramatically reversed when N,N-dibenzyl-protected amine aldehydes are used. Diastereomeric ratios are consistently 99:1 in favor of the Cram-type product.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja00194a033