Synthesis of spiro[indoline-3,2′-pyrrolidine] derivatives from β-3-indolyl ketone oximes

Chemistry Letters

Volumn 33, Issue 1, 2004, Pages 26-27

  Tanaka, Kenichi ^a   Mori, Yutaka ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; INDOLE DERIVATIVE; KETONE DERIVATIVE; METHANESULFONYL CHLORIDE; NITROGEN; OXIME DERIVATIVE; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; DRUG SYNTHESIS; METHODOLOGY;

EID: 2042547371     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.26     Document Type: Article

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25. In this manuscript, syn and anti isomer of oxime derivatives are defined when the hydroxy group on the oxime nitrogen is oriented syn and anti to the nucleophilic moiety, respectively.
26. Trapping of the 3a with other electrophiles such as acetyl chloride, trifluoroacetic anhydride, benzyloxycarbonyl chloride, and p-toluenesulfonyl chloride gave the complex mixture of products.
27. Compound 4a, 5b, and 3e were obtained as a mixture of two diastereomers, while compound 5a and 5c were obtained as a single diastereomer. The stereochemistry of 5a-c has not been determined.
28. Yields of the oximes 1a-e: 1a, 95% (anti:syn = 3:1). 1b, 92% (anti:syn = 3:1). 1c, 96% (anti:syn = 4:1). 1d, 95% (anti:syn = 3:1). 1e, 95% (anti.syn = 7:2).