Strategies for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates

Haruhiko Fuwa; Makoto Sasaki

doi:10.1021/ol071312a

Strategies for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates

Haruhiko Fuwa, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Tohoku University

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

Strategies have been developed for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates. A highly chemoselective cross-coupling of N-(o-bromophenyl)-α- phosphoryloxyenecarbamates with boron nucleophiles enabled the efficient preparation of various N-(o-bromophenyl)enecarbamates, which served as useful precursors for subsequent Heck-type cyclization or 5-endo-trig aryl radical cyclization to furnish 2-substituted indoles or indolines, respectively.

Original language	English
Pages (from-to)	3347-3350
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol071312a
Publication status	Published - 2007 Aug 16

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abstract = "Strategies have been developed for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates. A highly chemoselective cross-coupling of N-(o-bromophenyl)-α- phosphoryloxyenecarbamates with boron nucleophiles enabled the efficient preparation of various N-(o-bromophenyl)enecarbamates, which served as useful precursors for subsequent Heck-type cyclization or 5-endo-trig aryl radical cyclization to furnish 2-substituted indoles or indolines, respectively.",

author = "Haruhiko Fuwa and Makoto Sasaki",

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AB - Strategies have been developed for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates. A highly chemoselective cross-coupling of N-(o-bromophenyl)-α- phosphoryloxyenecarbamates with boron nucleophiles enabled the efficient preparation of various N-(o-bromophenyl)enecarbamates, which served as useful precursors for subsequent Heck-type cyclization or 5-endo-trig aryl radical cyclization to furnish 2-substituted indoles or indolines, respectively.

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Strategies for the synthesis of 2-substituted indoles and indolines starting from acyclic α-phosphoryloxy enecarbamates

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