Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes

Pin Sheng Lee; Naohiko Yoshikai

doi:10.1021/ol503119z

Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes

Pin Sheng Lee, Naohiko Yoshikai

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

102 Citations (Scopus)

Abstract

A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps. (Chemical Equation Presented).

Original language	English
Pages (from-to)	22-25
Number of pages	4
Journal	Organic letters
Volume	17
Issue number	1
DOIs	https://doi.org/10.1021/ol503119z
Publication status	Published - 2015 Jan 2
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol503119z

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abstract = "A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps. (Chemical Equation Presented).",

author = "Lee, {Pin Sheng} and Naohiko Yoshikai",

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AB - A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps. (Chemical Equation Presented).

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Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes

Abstract

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