ANIONIC HETERO[3, 3]REARRANGEMENTS. N, O-DIACYLHYDROXYLAMINES TO SUCCINIC ACID DERIVATIVES

N, O-Diacylhydroxylamines rearrange under basic conditions to afford 2, 3-disubstituted succinic acid derivatives. The rearrangement can be rationalized in terms of [3, 3]sigmatropic shifts of ester-amide dienolated N, O-diacylhydroxylamines.

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Bibliographic Details
Published in	Chemical & pharmaceutical bulletin Vol. 42; no. 2; pp. 419 - 421
Main Authors	UCHIDA, Takuya, ENDO, Yasuyuki, HIZATATE, Shoji, SHUDO, Koichi
Format	Journal Article
Language	English
Published	TOKYO The Pharmaceutical Society of Japan 1994 公益社団法人日本薬学会 Pharmaceutical Soc Japan Maruzen Japan Science and Technology Agency
Subjects	[3, 3]sigmatropic rearrangement Aliphatic compounds C-C bond formation Chemistry Chemistry, Medicinal Chemistry, Multidisciplinary enolate Exact sciences and technology Life Sciences & Biomedicine N, O-diacylhydroxylamine Organic chemistry Pharmacology & Pharmacy Physical Sciences Preparations and properties Science & Technology N,O-DIACYLHYDROXYLAMINE ESTERS ENOLATE C-C BOND FORMATION [3,3]SIGMATROPIC REARRANGEMENT CLAISEN REARRANGEMENT CATALYZED REARRANGEMENT Sigmatropic reaction Dicarboxylic acid Aliphatic compound Enolate Organic hydroxylamine
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ISSN	0009-2363 1347-5223
DOI	10.1248/cpb.42.419

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Summary:	N, O-Diacylhydroxylamines rearrange under basic conditions to afford 2, 3-disubstituted succinic acid derivatives. The rearrangement can be rationalized in terms of [3, 3]sigmatropic shifts of ester-amide dienolated N, O-diacylhydroxylamines.
Bibliography:	ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 14
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.42.419