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Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

ABSTRACT: Problem solved: the title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines. Stereocenter formation is believed to occur by enantioselective cis?aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence.

SUBMITTER: Bovino MT

PROVIDER: S-EPMC3324620 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Bovino Michael T MT Chemler Sherry R SR

Angewandte Chemie (International ed. in English) 20120305 16

Problem solved: the title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines. Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence. ...[more]

PMID: 22392873

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